反应 #2200581

反应方程式

TEMPO

(2R,3S)-2-methyl-3-tetrahydropyranyloxybutanol

NaOCl

NaHCO3

sodium bromide

→

aldehyde

收率 92.3%

(2S,3S)-2-methyl-3-tetrahydropyranyloxybutyraldehyde

收率 92.3%

溶剂

toluene

EtOAc

H2O

反应条件

后处理

1. 1
   其他The aqueous phase was separated
2. 2
   洗涤washed with Et2O (50 ml)
3. 3
   洗涤The combined organic phases were washed with a KI solution (80 mg)
4. 4
   workup.DISSOLUTIONdissolved in aqueous 10% KHSO4 (20 ml)
5. 5
   干燥with a 10% aqueous sodium thiosulfate solution (10 ml), brine (20 ml), and dried (MgSO4)
6. 6
   过滤Filtration and concentration under vacuum

实验过程

An aqueous NaOCl solution (11 mmol, 5.3 ml of a 12.5% solution) and NaHCO3 (2.43 g, 29 mmol) was added dropwise, over a period of 1 hour, to a cold (0° C.), rapidly stirred (>1000 rpm), biphasic mixture consisting of (2R,3S)-2-methyl-3-tetrahydropyranyloxybutanol (5) (1.88 g, 10 mmol), TEMPO with free radicals (31.25 mg, 2%), sodium bromide (1.029 g, 10 mmol), toluene (30 ml), EtOAc (30 ml) and H2O (5 ml). The aqueous phase was separated and washed with Et2O (50 ml). The combined organic phases were washed with a KI solution (80 mg) dissolved in aqueous 10% KHSO4 (20 ml), and then with a 10% aqueous sodium thiosulfate solution (10 ml), brine (20 ml), and dried (MgSO4). Filtration and concentration under vacuum gave the desired aldehyde 6 (1.72 g, 92%) which was used for the next reactions without further purification.

来源