Triethylamine → Methyl toluenesulfonyloxyacetate

HRID 1940259

反応式

HRID 1940259 の反応式
[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

参加物

5

反応物 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 66774Methyl Glycolate

生成物 1

HCID 86751745Methyl toluenesulfonyloxyacetate収率 98.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-49cbc3da55944ccc97d427074c032aa5
出典データセット
uspto-grants-1997_12
特許番号
US05698735

関連ノート

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