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9th August 2013 @ 12:19

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SOURCE

Author 1 is the author of this LabTrove post (and has contributor role of "Abstracter").

  *First name *Last name Email Organization Role
Author 2 Jozef Stec   University of Southampton Doer
Author 3 Richard Whitby   University of Southampton Conciever
Author 4          

TEXT

*Procedure or Transformation Copper-catalysed Mannich reaction to afford N-allyl-N-benzylamine
*Compound(s) being made N-allyl-N-benzylamine
*Chemicals used (delimited by semicolons ;) N-Allylamine; Benzyl bromide
*Procedure

Benzyl bromide (13.9 mL, 0.117mol) was added dropwise to neat allylamine (52.7 mL, 0.702 mol) at ~-5oC. The reaction mixture was then allowed to warm to room temperature and was stirred for a further 16 hours

After this time, the reaction mixture was cooled to 0oC and quenched with sat. NaHCO3 (aq) (200 mL). Extraction with Et2O (3 x 100 mL). The combined organic phases were washed with H2O (3 x 200 mL) and brine (200 mL). Concentration in vacuo gave a yellow oil.

Purification of the crude material by column chromatography on SiO2 (for flash chromatography) and 1:1 Et2O in hexanes. The final product was a yellow oil (77.5%)

*Authors Comments GC[SDFASTD] after 16 hours showed main peak at 2.964 minutes (90% product) and at 5.77 minutes (100%). (Probably the product of double benzylation)
Lead Reference J. Stec, 2009, "Tandem Reaction Sequences on a Zirconocene Template",PhD thesis, University of Southampton
Other References Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268-2272.
Multimedia Content -
*Data HNMR
#Data file 1 http://blogs.chem.soton.ac.uk/data/36519.html
#Data file 2  
#Data file 3  
#Data file 4  
#Data file 5  

SCHEME

*#Structure file (ChemDraw, ChemSketch or RXN file)
ReactionScheme.cdx
 
*#Image file (GIF or PNG)
ReactionScheme.gif

Keywords

Compounds Keywords Amines; Alkanes; Alkenes
Reactions Keywords  
Other Keywords Mannich
Attached Files
9th August 2013 @ 11:55

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Compound

ChemSpider ID 454584
*#Name of Compound mol file
2.59.mol
 

Description and Tags

Description  
Tags (separated by comma)  

Identifiers

*Chemical Name N-allyl-N-benzylamine
Common Name  
Synonym  

Spectra

  *#Spectrum jcamp file *Spectrum Type Comments OpenData Image or PDF
Spectrum 1
HNMR.jdx
 
HNMR 1HNMR
HNMR.pdf
 
Spectrum 2
CNMR.jdx
 
CNMR  13CNMR
CNMR.pdf
 
Spectrum 3
DEPT.jdx
 
CNMR  DEPT-135
DEPT.pdf
 
Spectrum 4          
Spectrum 5          
Spectrum 6          
Spectrum 7          
Spectrum 8          
Spectrum 9          
Spectrum 10          

Properties

Experimental Physico-chemical Properties

Property Value Unit Comments
Experimental Boiling Point      
Experimental Flash Point      
Experimental Freezing Point      
Experimental Gravity      
Experimental Ionization Potent      
Experimental LogP      
Experimental Melting Point      
Experimental Optical Rotation      
Experimental Refraction Index      
Experimental Solubility      
Experimental Vapor Pressure      
Non Water Solubility      
Non Water Solubility      

Spectroscopy

Property Value Unit Comments
Lambda Max      

Miscellaneous

Property Value Unit Comments
Appearance Yellow Oil    
Bio Activity      
Chemical Class      
Compound Source      
Drug Status      
Exposure Limits      
Exposure Limits Niosh Rel      
Exposure Routes      
First-Aid      
Incompatability      
Personal Protection      
Safety      
Stability      
Symptoms      
Target Organs      
Therapeutical Effect      
Toxicity      
Attached Files
9th August 2013 @ 11:29

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SOURCE

Author 1 is the author of this LabTrove post (and has contributor role of "Abstracter").

  *First name *Last name Email Organization Role
Author 2 Jozef Stec   University of Southampton Doer
Author 3 Richard Whitby   University of Southampton Conciever
Author 4          

TEXT

*Procedure or Transformation Lithiation of alkyne and then S
*Compound(s) being made 10-(tert-butyldimethylsiloxy)-1-decen-6-yn
*Chemicals used (delimited by semicolons ;) tert-butyldimethyl(pent-4-yn-1-yloxy)silanenBuLi; HMPA; 5-bromo-1-pentene; THF
*Procedure

To a stirred solution of tert-butyldimethyl(pent-4-yn-1-yloxy)silane (0.99 g, 5.0 mmol) in dry THF (10 mL) at -78oC was added dropwise nBuLi (20 mL, 5.0 mmol). The reaction was stirred for a further hour during which HMPA (0.87 mL, 5.0 mmol) was added dropwise and the reaction mixture was allowed to warm to -40oC. Then, a solution of 5-bromo-1-pentene (0.56 mL, 5.0 mmol) in dry THF was added and the stirring was continued for 1 hour during which the reaction mixture was allowed to warm to -10oC. After this time, the stirring was continued for 24 hours at room temperature. The reation mixture was then quenched with sat NH4Cl (aq) and the products were extracted into Et2O. Drying over MgSO4 followed by concentration in vacuo gave the crude material as a yellow oil.

Purification of the crude material by column chromatography on SiO2 (for flash chromatography) and 3% of Et2O in hexanes as the eluent. The final product was a yellow oil (combined yield 65%)

*Authors Comments Reaction of lithiated tert-butyldimethyl(pent-4-ynyloxy)silane with 5-bromo-1-pentene gave an inseparable mixture of two compounds in the ratio of 2 : 1 respectively and 63% combined yield. The undesired product resulted from the nucleophilic attack of the lithiated alkyne onto silyl group.
Lead Reference J. Stec, 2009, "Tandem Reaction Sequences on a Zirconocene Template",PhD thesis, University of Southampton
Other References Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207.
Multimedia Content -
*Data HNMR
#Data file 1 http://blogs.chem.soton.ac.uk/data/36483.html
#Data file 2  
#Data file 3  
#Data file 4  
#Data file 5  

SCHEME

*#Structure file (ChemDraw, ChemSketch or RXN file)
ReactionScheme.cdx
 
*#Image file (GIF or PNG)
ReactionScheme.gif
 

Keywords

Compounds Keywords Alkanes, Alkenes, Alkynes, Ethers
Reactions Keywords  
Other Keywords Protection
Attached Files
9th August 2013 @ 10:28

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Compound

ChemSpider ID  
*#Name of Compound mol file
2.54.mol
 

Description and Tags

Description  
Tags (separated by comma)  

Identifiers

*Chemical Name 10-(tert-butyldimethylsiloxy)-1-decen-6-yn
Common Name  
Synonym  

Spectra

  *#Spectrum jcamp file *Spectrum Type Comments OpenData Image or PDF
Spectrum 1
HNMR.jdx
 
HNMR 1HNMR Y
HNMR.pdf
 
Spectrum 2
CNMR.jdx
 
CNMR  13CNMR 
CNMR.pdf
 
Spectrum 3
DEPT135.jdx
 
CNMR  DEPT-135
DEPT135.pdf
Spectrum 4   2D NMR 1H-1H COSY COSY 1H-1H 
COSY.pdf
 
Spectrum 5          
Spectrum 6          
Spectrum 7          
Spectrum 8          
Spectrum 9          
Spectrum 10          

Properties

Experimental Physico-chemical Properties

Property Value Unit Comments
Experimental Boiling Point      
Experimental Flash Point      
Experimental Freezing Point      
Experimental Gravity      
Experimental Ionization Potent      
Experimental LogP      
Experimental Melting Point      
Experimental Optical Rotation      
Experimental Refraction Index      
Experimental Solubility      
Experimental Vapor Pressure      
Non Water Solubility      
Non Water Solubility      

Spectroscopy

Property Value Unit Comments
Lambda Max      

Miscellaneous

Property Value Unit Comments
Appearance Pale Yellow Oil    
Bio Activity      
Chemical Class      
Compound Source      
Drug Status      
Exposure Limits      
Exposure Limits Niosh Rel      
Exposure Routes      
First-Aid      
Incompatability      
Personal Protection      
Safety      
Stability      
Symptoms      
Target Organs      
Therapeutical Effect      
Toxicity      
Attached Files
9th August 2013 @ 10:09

This post is compatible for submission to ChemSpider SyntheticPages.

See ChemSpider SyntheticPages style reaction template - help and further information for help when using it.

SOURCE

Author 1 is the author of this LabTrove post (and has contributor role of "Abstracter").

  *First name *Last name Email Organization Role
Author 2 Jozef Stec   University of Southampton Doer
Author 3 Richard Whitby   University of Southampton Conciever
Author 4          

TEXT

*Procedure or Transformation TBDMS protection of 1-phenylhept-6-en-1-yn-3-ol
*Compound(s) being made (1-phenylhept-6-en-1-yn-3-yloxy)(tert-butyl)dimethylsilane
*Chemicals used (delimited by semicolons ;) 1-phenylhept-6-en-1-yn-3-ol; Et3N; TBDMSOTf; DCM
*Procedure

To a solution of 1-phenylhept-6-en-1-yn-3-ol (0.556 g, 2.98 mmol) in dry CH2Cl2 (25 mL) was added Et3N (1025 mL, 9.0 mmol) at 0oC. After stirring for 5 minutes; TBDMSOTf (1.05 mL, 4.5 mmol) was added and the stirring was continued at 0oC for 10 minutes after which the cooling bath was removed and the reaction mixture was stirred for 50 minutes at room temperature. Then, the reaction mixture was quenched with H2O (20 mL) and the whole mixture was poured onto H2O (100 mL) and extracted with CH2Cl2 (2 x 75 mL). The combined organic phases were washed with H2O and brine. Drying over MgSO4 followed by concentration in vacuo gave the crude product as a brown oil.

Purification of the crude material was performed by column chromatography on Al2O3 (basic, grade III) and hexan as the eluent gave a pure material as a pale yellow oil (73.5%) 

*Authors Comments TBDMS protection of the hydroxyl group gave the co-cyclisation precursor
Lead Reference J. Stec, 2009, "Tandem Reaction Sequences on a Zirconocene Template",PhD thesis, University of Southampton
Other References Krafft, M. E.; Boñaga, L. V. R.; Hirosawa, C. J. Org. Chem. 2001, 66, 3004-3020.
Multimedia Content -
*Data HNMR
#Data file 1  http://blogs.chem.soton.ac.uk/data/36459.html
#Data file 2  
#Data file 3  
#Data file 4  
#Data file 5  

SCHEME

*#Structure file (ChemDraw, ChemSketch or RXN file)
ReactionScheme.cdx
 
*#Image file (GIF or PNG)
ReactionScheme.gif
 

Keywords

Compounds Keywords Alkanes, Alkenes, Alkynes, Aromatics/Arenes
Reactions Keywords  
Other Keywords Protection
Attached Files