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30th August 2013 @ 16:40

 

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Reaction information

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

To a solution of 3,4-dihydro-2H-pyran (631 mg, 7.5 mmol) in THF (8 mL) at –40 °C under Ar, is added dropwise tert-butyllithium (6.1 mL of a 1.3 M solution in pentanes, 8 mmol). The solution is allowed to warm to 0 °C and stirred for 30 minutes before cooling to –20 °C and treatment with a solution of the 1-iodo-4-pentene (980 mg, 5 mmol) in THF (2 mL). The yellow reaction mixture is allowed to warm to RT and heated at reflux for 1 h. The solution is allowed to cool and poured into saturated NaHCO3 solution (10 mL) and pentane (20 mL). The aqueous layer is separated and extracted with pentane (3 x 50 mL), and the combined organic phases dried over Na2SO4, filtered and concentrated. The crude product was purified by Kugelrohr distillation (75 °C, 0.4 mbar) to give the desired product as a clear, colourless oil (693 mg, 4.56 mmol, 91%).

*Yield (%) 91
*Type of Yield Isolated Product Yield 
Reference(s)

P. J. Kocienski, M. Pritchard, S. N. Wadman, R. J. Whitby, C. L. Yeates, J. Chem. Soc. Perkin Trans. 1 1992, 24, 3419.

DavidOwenThesis2000pp42,43,102,103.pdf
305LABBOOK.JPG
 
Further information Compound 305: 2-(4-Pentenyl)-5,6-dihydro-4H-pyran

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 

Stoichiometry Table of Substances Used/Produced

Compound Information Substance Information Planned Amounts Actual Amounts
ChemSpider ID: 9162369
Name: 5-Iodo-1-pentene
Formula: C_{5}H_{9}I
MW: 196
compound image
Safety Information:
Role: limiting reactant
State: solution
Source:
Molarity: Moles/L
Concentration: 7.95 g/L
Solvent: THF
Comments:
Ratio: 1.00
Amount: 0.00500 Moles*
Mass: 0.980 g
Volume: 0.123 L
Ratio: 1.00
Amount: 0.00500 Moles*
Mass: 0.980 g
Volume: 0.123 L
ChemSpider ID: 7789
Name: 3,4-Dihydro-2H-pyran
Formula: C_{5}H_{8}O
MW: 84.1
compound image
Safety Information:
Role: reactant
State: solution
Source:
Molarity: 11.79 Moles/L
Concentration: g/L
Solvent: THF
Comments:
Ratio: 2.80
Amount: 0.0140 Moles*
Mass: 1.18 g
Volume: 0.00119 L
Ratio: 2.80
Amount: 0.00750 Moles*
Mass: 0.631 g
Volume: 0.000636 L
ChemSpider ID: 10254347
Name: t-BuLi
Formula: C_{4}H_{9}Li
MW: 64.1
compound image
Safety Information:
Role: reactant
State: solution
Source:
Molarity: 1.7 Moles/L
Concentration: g/L
Solvent:
Comments:
Ratio: 1.60
Amount: 0.00800 Moles*
Mass: 0.512 g
Volume: 0.00471 L
Ratio: 1.60
Amount: 0.00600 Moles*
Mass: 0.384 g
Volume: 0.00353 L
ChemSpider ID: 29341335
Name: 6-(4-Penten-1-yl)-3,4-dihydro-2H-pyran
Formula: C_{10}H_{16}O
MW: 152
compound image
Safety Information:
Role: product
State: liquid
Source:
Purity: 100%
Comments:
Ratio: 1.00 *
Amount: 0.00500 Moles
Mass: 0.761 g
Ratio: 1.00
Amount: 0.00456 Moles*
Mass: 0.694 g
Yield: 91.2 %

(* indicates entered value)

Attached Files
ReactionScheme.gif
ReactionScheme.cdx
DavidOwenThesis2000pp42,43,102,103.pdf
305LABBOOK.JPG