4-Toluenesulfonyl chloride → toluene-4-sulfonic acid (S)-2-(3-chlorophenyl)-2-hydroxyethyl ester

HRID 929081

反応式

HRID 929081 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:11])[CH2:9][O:10][S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10130180(S)-1-(3-Chlorophenyl)ethane-1,2-diol

生成物 1

HCID 15442725toluene-4-sulfonic acid (S)-2-(3-chlorophenyl)-2-hydroxyethyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a mixture of (S)-1-(3-Chloro-phenyl)-ethane-1,2-diol (9.83 g, 0.057 mol) and triethylamine (11.8 ml, 0.086 mol) a solution of TsCl (10.87 g, 0.057 mol) in dichloromethane (50 mL) was added at 0° C. over 30 min. The mixture was stirred at 0° C. for 4 h. Precipitate formed was removed by filtration, the filtrate was washed with water (50 mL), dried over Na2SO4 and evaporated. The residue was dissolved in CH2Cl2 (200 mL), filtered through a SiO2 pad and evaporated. Colorless oil, 16.34 g (0.050 mol, 88%).

後処理

  1. additionwas added at 0° C. over 30 min
  2. customPrecipitate formed
  3. customwas removed by filtration
  4. washthe filtrate was washed with water (50 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. dissolutionThe residue was dissolved in CH2Cl2 (200 mL)
  8. filtrationfiltered through a SiO2 pad
  9. customevaporated

出典と根拠

ORDレコード
ord-a6089a877bf340c193ab6f7c58a3ddf3
出典データセット
uspto-grants-2016_03
特許番号
US09290503B2

関連ノート

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