Dimethyl Sulfoxide → (3-Ethyl-4-methyl-cyclohex-3-enyl)-acetaldehyde

Participants

Reaction Steps

The deprotected alcohol was oxidized by the standard “Swern” procedure (Mancuso, Synthesis 1981 p165, incorporated herein by reference) as follows: The alcohol (5 mmol) was added to a solution of oxalyl chloride (3.5 mL, 7.0 mmol) in CH2Cl2 (30 mL) with DMSO (0.64 mL, 9.0 mmol) at −78° C. After 40 min., NEt3 (2.50 mL) was added and the mixture was warmed to rt. After standard aqueous work-up and purification, (3-ethyl-4-methyl-cyclohex-3-enyl)-acetaldehyde (Intermediate K5) was isolated (˜90%).

Provenance & Evidence