反应详情

To a solution of (−)-2-(4-bromophenyl)-3-hydroxypropyl acetate (5.88 g, 21.5 mmol) in dichloromethane (100 ml) was added triethylamine (5.45 g, 53.8 mmol), p-toluenesulfonyl chloride (4.93 g, 25.8 mmol) and 4-dimethylaminopyridine (0.263 g, 2.15 mmol) at 0° C. The mixture was stirred at room temperature for 2 hours and partitioned between saturated ammonium chloride solution and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=4/1) to afford (+)-3-acetoxy-2-(4-bromophenyl)propyl 4-methyl-benzenesulfonate as colorless oil (8.32 g, 90%). [α]D=+1.63 (C=0.5, CHCl3).

1. custompartitioned between saturated ammonium chloride solution and dichloromethane
2. washThe organic layer was washed with brine
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=4/1)