반응 #2200581

반응 방정식

TEMPO

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

NaOCl

NaHCO3

sodium bromide

→

aldehyde

수율 92.3%

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

수율 92.3%

용매

toluene

EtOAc

H2O

반응 조건

후처리

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

실험 절차

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.

출처