Water → HCID 57857017, compound

Participants

Reaction Steps

(Z)-7-((1R,2R,5S)-2-((R,E)-3-(Benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)prop-1-enyl)-3-methylene-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid (19a, limiting reagent) is dissolved in THF (0.3 M) under a nitrogen atmosphere. A solution consisting of TBAF in THF (1.2 molar equivalents, 1 M) is added and the reaction mixture is stirred at room temperature. Upon completion, as judged by TLC, water is added and most of the THF is removed under reduced pressure. The remaining aqueous solution is extracted with ethyl acetate and is washed with water and brine. The organic phase is dried over sodium sulfate, filtered, and the solvent is evaporated. The crude product is purified by flash chromatography on regular silica gel eluted with hexanes-ethyl acetate (+0.4% acetic acid) to afford the title intermediate.

Provenance & Evidence