反应详情

To a cold (ice bath) mixture of (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclopentanecarboxylic acid ethyl ester (epimeric mixture, 250 mg), 4-chlorophenol (136 mg) and triphenylphoshine (256 mg) in dichloromethane (4 mL) and tetrahydrofuran (1.5 mL) was slowly added a solution of di-tert-butyl-azodicarboxylate (225 mg) in tetrahydrofuran (2.5 mL). The reaction mixture was stirred at room temperature for 2.5 days then concentrated in vacuo and the residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/ethylacetate (1:0 to 9:1 v/v) as eluant to afford the title compound (0.304 g, 89%) as light yellow oil. MS (EI): 413.2 (M+H)+.

1. concentrationthen concentrated in vacuo
2. customthe residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/ethylacetate (1:0 to 9:1 v/v) as eluant