反应详情

温度

-70 °C

2-Methylthiophenylmethylmagnesium chloride was prepared from magnesium turnings (654 mg) and 2-(chloromethyl)thioanisole (1.55 g) in ether (29 ml) by the method of J. Am. Chem. Soc. (1943) 65, 295. A solution of lithium chloride (38 mg) and copper(II) chloride (60 mg) in THF (2.8 ml) was added dropwise to the ethereal solution of the Grignard reagent followed by addition of a solution of (2RS,3S)-3-(benzyloxy)-1,2-epoxybutane (0.8 g) in ether (8 ml) below −60° C. The mixture was stirred at −70° C. for 1 h, and then allowed to warm to room temperature and stirred overnight. After cooling, the mixture was quenched with saturated aqueous ammonium chloride solution (22 ml). The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give an oil. Column chromatography (CH2Cl2) over silica gel gave a pale brown oil of (2S,3S)-2-benzyloxy-5-(2-(methylthio)phenyl)pentan-3-ol (0.65 g, 45.8%).

1. temperatureto warm to room temperature
2. stirringstirred overnight
3. temperatureAfter cooling
4. customthe mixture was quenched with saturated aqueous ammonium chloride solution (22 ml)
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated in vacuo
8. customto give an oil