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

HRID 470314

反応式

HRID 470314 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, evaporated. The residue vas dissolved in CH2Cl2 (200 ml), filtered through a SiO2 pad, evaporated. Colorless oil, 16.34 g (0.050 mol, 88%). 1H NMR (300 MHz, DMSO) δ 7.67 (d, J=8.5 Hz, 2H), 7.42 (d, J=8.5 Hz, 2H), 7.20-7.35 (m, 4H), 5.90 (d, J=4.9 Hz, 1H), 4.79 (q, J=5.1 Hz, 1H), 4.03 (m, 2H), 2.41 (s, 3H)

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 vas dissolved in CH2Cl2 (200 ml)
  8. filtrationfiltered through a SiO2 pad
  9. customevaporated

出典と根拠

ORDレコード
ord-6712fe730cb54016a36539127c6af5fa
出典データセット
uspto-grants-2014_01
特許番号
US08629147B2

関連ノート

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