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16th September 2013 @ 15:16

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Reaction information

*#Reaction file
OverallReactionScheme.cdx
 
*Reaction file type CDX 
*Procedure See Child Reaction Steps 
*Yield (%) N/A 
*Type of Yield N/A 
Reference(s)
Thesis L Sayer10-11.pdf
 
Further information

For multistep reactions (or their steps):

Overall reaction? True 
For overall reaction - links to child reaction steps Reaction 73
Reaction 32 
For step in multistep reaction - link to previous reaction step N/A 
For step in multistep reaction - link to following reaction step N/A 
Attached Files
9th September 2013 @ 10:35

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Reaction information

*#Reaction file
OverallReaction.cdx
 
*Reaction file type CDX 
*Procedure See Child Reaction Steps 
*Yield (%) N/A 
*Type of Yield N/A 
Reference(s)
DavidOwenThesis2000pp82,83,171,172.pdf
 
Further information Compound 430: 7-[4,4-Di(methoxymethyl)-2-methylcyclopentyl]-1-heptanol 

For multistep reactions (or their steps):

Overall reaction? True 
For overall reaction - links to child reaction steps Reaction 429
Reaction 430 
For step in multistep reaction - link to previous reaction step N/A 
For step in multistep reaction - link to following reaction step N/A 
Attached Files
9th September 2013 @ 10:32

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Reaction information

*#Reaction file
ReactionScheme.cdx
 
*Reaction file type CDX 
*Procedure

To a solution of tert-butyl[2-(2-{(E)-4-[4,4-di(methoxymethyl)-2-methylcyclo pentyl]-2-butenyl}-1,3-dithian-2-yl)ethoxy]dimethylsilane (117 mg, 0.23 mmol) in THF (3 mL) was added dropwise tetrabutyl ammonium fluoride (0.35 mL of a 1 M solution in THF, 0.35 mmol). The mixture was stirred for 1 h, before being quenched with water (5 mL). The solution was diluted with ether, and the aqueous phase extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. To the crude product was added ethanol (5 mL) and Raney nickel (10 g of a 1:1 slurry in water). The mixture was heated at reflux for 2 h, then filtered through a sinter, with ether and water washing. The phases of the filtrate were separated and the aqueous extracted with ether. The combined extracts were washed with brine, dried over MgSO4 and concentrated. Purification of the crude product by column chromatography (SiO2, 20% ether in petrol) yielded the title compound (31 mg, 0.11 mmol, 47%).

*Yield (%) 47 
*Type of Yield Isolated Product Yield 
Reference(s)
DavidOwenThesis2000pp82,83,171,172.pdf
 
Further information Compound 430: 7-[4,4-Di(methoxymethyl)-2-methylcyclopentyl]-1-heptanol 

For multistep reactions (or their steps):

Overall reaction? False 
For overall reaction - links to child reaction steps N/A
For step in multistep reaction - link to previous reaction step Reaction 429 
For step in multistep reaction - link to following reaction step N/A 
Attached Files
9th September 2013 @ 10:30

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Reaction information

*#Reaction file
ReactionScheme.cdx
 
*Reaction file type CDX 
*Procedure

n-Butyllithium (0.21 mL of a 2.5 M solution in hexanes, 0.525 mmol) was added dropwise to a solution of 2-{(E)-4-[4,4-di(methoxymethyl)-2-methylcyclopentyl]-2-butenyl}-1,3-dithiane (427) in THF (3 mL) under Ar at –40 °C. The reaction was stirred for 2 h and allowed to warm to –20 °C. After cooling to –78 °C, HMPA (0.2 mL) was added, resulting in a bright yellow suspension, which was decolourised on addition of a solution of (2-iodoethoxy)-tert-butyl dimethyl silane (143 mg, 0.5 mmol) in THF (1 mL).  After 30 min, the solution was allowed to warm to room temperature and stirred over night. The reaction mixture was poured into water and ether, and the aqueous layer extracted with ether. The combined organic phases were washed with brine, dried over MgSO­4, filtered and concentrated. Column chromatography (SiO2, 10% ether in petrol) furnished the desired compound as a viscous, colourless oil (141 mg, 0.28 mmol, 56%) contaminated with a small amount of an inseparable impurity.

*Yield (%) 56 
*Type of Yield Reaction Yield 
Reference(s)
DavidOwenThesis2000pp82,83,170,171.pdf
429LABBOOK.JPG
 
Further information Compound 429: tert-Butyl[2-(2-{(E)-4-[4,4-di(methoxymethyl)-2-methylcyclopentyl]-2-butenyl}-1,3-dithian-2-yl)ethoxy]dimethylsilane 

For multistep reactions (or their steps):

Overall reaction? False 
For overall reaction - links to child reaction steps N/A 
For step in multistep reaction - link to previous reaction step N/A 
For step in multistep reaction - link to following reaction step Reaction 430
Attached Files
9th September 2013 @ 10:22

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Reaction information

*#Reaction file
ReactionScheme.cdx
 
*Reaction file type CDX 
*Procedure Ethylene oxide (1 mL of 1:1 solution in ether, 10 mmol) was added to a solution of TBDMSCl (1.507 g, 10 mmol) and NaI (1.5 g, 10 mmol) in MeCN (1.5 mL) under Ar at 0 oC. After an hour the solution was poured into H2O and ether. Extracted into ether/pentane. The extracts were washed with Na2S2O3 and brine. Then it was dried over MgSO4 and concentrated.
The crude product was then columned (20% ether) to produce the desired compound (1.196 g, 42%) 
*Yield (%) 42 
*Type of Yield Reaction Yield 
Reference(s)
DavidOwenThesis2000pp82,83,170.pdf
 
Further information Compound 428: (2-Iodoethoxy)-tert-butyldimethylsilane 

For multistep reactions (or their steps):

Overall reaction? True 
For overall reaction - links to child reaction steps N/A 
For step in multistep reaction - link to previous reaction step N/A 
For step in multistep reaction - link to following reaction step N/A 
Attached Files