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2nd September 2013 @ 09:45

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Reaction information

*#Reaction file
*Reaction file type CDX 

To a solution of oxalyl chloride (1.752 g, 13.8 mmol) in DCM (70 mL) at –80 °C under Ar was added dimethylsulfoxide (1.900 g, 24.3 mmol). After 30 min, a –78 °C solution of 3-phenyl-pent-4-en-1-ol (1.312 g, 8.1 mmol) in DCM (20 mL) was added, resulting in a white suspension. After 40 min at –80 °C triethylamine (3.28 g, 32.4 mmol) was added and the solution allowed to warm to RT. The reaction mixture was diluted with saturated NaHSO4 solution and extracted into DCM. The extracts were washed with saturated NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated. The crude compound was purified by column chromatography (Al2O3, 10% ether in petrol) to give the desired product (1.070 g, 83%). 

*Yield (%) 83
*Type of Yield Isolated Product Yield 

K. Omura, D. Swern, Tetrahedron 1978, 34, 1651.

Further information

The title compound was prepared by standard Swern oxidation conditions.

Compound 322: 3-Phenyl-pent-4-enal

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 319 
For step in multistep reaction - link to following reaction step Reaction 323
Attached Files