4-Toluenesulfonyl chloride → (R)-Toluene-4-sulfonic acid 2-(6-chloro-pyridin-3-yl)-2-hydroxy-ethyl ester
反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:11])[CH2:9][O:10][S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])=[CH:4][CH:3]=1参加物
4
反応条件
- 温度
- 50 °C
実験手順
To a cooled (50° C.), stirred solution of (R)-1-(6-chloro-pyridin-3-yl)-ethane-1,2-diol (17.8 g) in anhydrous pyridine (100 mL) was added p-toluenesulfonyl chloride (19.5 g) in one portion. After 20 min, the cooling bath was removed and stirring was continued an additional 2 h. The reaction solution was concentrated in vacuo, azeotroped with toluene (2×), diluted in ethyl acetate, washed with half-saturated aqueous brine, saturated aqueous brine, dried over sodium sulfate and concentrated in vacuo. The resulting solids were recrystallized from ethyl acetate/hexanes to afford 23.3 g of the title compound (I-2d) as colorless crystals.