反应详情

温度

0 °C

To a solution of 2-chlorobenzenthiol (306 mg) in tetrahydrofuran (4 mL) was added a suspension of sodium hydride in oil (55% w/w, 107 mg). The white suspension was cooled down to 0° C. then a solution of (1R,2R)-2-(4-Chloro-phenoxymethyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester (epimeric mixture, 343 mg) in tetrahydrofuran (5 mL) was slowly added. The reaction mixture was stirred at room temperature for 4 days. Hydrochloric acid (1N) was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with an aqueous saturated solution of sodiumcarbonate and brine then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/ethylacetate (19:1 to 3:1 v/v) as eluant to afford the title compound (0.205 g, 53%) as light yellow oil. MS (EI): 424.0 (M+H)+.

1. extractionthe mixture was extracted with ethyl acetate
2. washThe combined organic layers were washed with an aqueous saturated solution of sodiumcarbonate and brine
3. dry with materialthen dried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/ethylacetate (19:1 to 3:1 v/v) as eluant