تفاعل #2200581

معادلة التفاعل

TEMPO

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

NaOCl

NaHCO3

sodium bromide

→

aldehyde

المردود 92.3%

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

المردود 92.3%

المذيبات

toluene

EtOAc

H2O

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر