Triethylamine → Methyl toluenesulfonyloxyacetate

HRID 1940259

반응식

HRID 1940259 반응식
[OH:1][CH2:2][C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.[C:14]1([CH3:24])[C:15]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1>ClCCl>[C:14]1([CH3:24])[C:15]([S:20]([O:1][CH2:2][C:3]([O:5][CH3:6])=[O:4])(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 66774Methyl Glycolate

생성물 1

HCID 86751745Methyl toluenesulfonyloxyacetate수율 98.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

18 g (0.2 mol) of methyl hydroxyacetate and 20.2 g (0.2 mol) of triethylamine are first introduced into 300 ml of dichloromethane at 0° C. 41.9 g (0.22 mol) of toluenesulfonyl chloride are then added at this temperature in small portions. Stirring of the batch at 0° C. is continued overnight. Ice water is added, the phases are separated, and the aqueous phase is extracted three times with dichloromethane. The combined organic phases are washed once with water, dried, and the solvent is removed on a rotary evaporator. 48 g (98% of theory) of methyl toluenesulfonyloxyacetate having a GC content of 96% are isolated as a colorless solid.

후처리

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted three times with dichloromethane
  3. washThe combined organic phases are washed once with water
  4. customdried
  5. customthe solvent is removed on a rotary evaporator

출처 및 근거

ORD 기록
ord-49cbc3da55944ccc97d427074c032aa5
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05698735

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