반응 #1480457

반응 방정식

alcohol

4-(2-benzyloxy-ethyl)-2-ethyl-1-methyl-cyclohexanol

NEt3

alcohol

4-(2-benzyloxy-ethyl)-2-ethyl-1-methyl-cyclohexanol

oxalyl chloride

DMSO

→

(3-ethyl-4-methyl-cyclohex-3-enyl)-acetaldehyde

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타Mancuso, Synthesis 1981 p165
2. 2
   기타After standard aqueous work-up and purification

실험 절차

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%).

출처