反应详情

To a mixture of 3-methylthio-1-propanol (17) (5.0 g, 47.1 mmol), pyridine (7.43 g, 94.0 mmol) and CHCl3 (47 mL) cooled in an ice bath, tosyl chloride (13.47 g, 70.6 mmol) was added in portions with stirring. The mixture was allowed to warm to room temperature after 1 hour and stirring was continued for an additional 15 hours. The mixture was diluted with CH2Cl2 (200 mL), washed with water (2×100 mL), and the organic phase as dried (Na2SO4). The solvent was evaporated and the resulting yellow oil purified by column chromatography (silica gel, 15 wt % ether/hexanes, 50 wt % ether/hexanes), to give a colorless oil (10.5 g, 86 wt %), namely 3-methylthio-1-propanol tosylate.

1. temperaturecooled in an ice bath
2. stirringstirring
3. washwashed with water (2×100 mL)
4. dry with materialthe organic phase as dried (Na2SO4)
5. customThe solvent was evaporated
6. customthe resulting yellow oil purified by column chromatography (silica gel, 15 wt % ether/hexanes, 50 wt % ether/hexanes)