Vinyl butyrate → (S)-3,3,3-Trifluoro-2-hydroxy-2-(hydroxymethyl)Propyl butanoate

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Reaction Steps

Vinyl butyrate (1 ml) was added to a stirred mixture of 4 Å molecular sieves (2 g), lipase Amano PS precipitate (100 mg) and 2-(trifluoromethyl)-1,2,3-propanetriol (1 g) suspended in 1,1-dimethylethyl methyl ether (10 ml) and the mixture stirred at room temperature. The mixture was filtered through celite after 21.5 hours, washing with dichloromethane, concentrated, diluted with toluene (20 ml) and washed with saturated aqueous sodium chloride (2×20 ml), dried (Na2SO4) and evaporated to give a light yellow oil. 19F NMR spectroscopy displayed a 20:1 mixture of monoester/diester with no starting triol. The yellow oil was purified by chromatography over silica using a 1:1 mixture of dichloromethane/cyclohexane as eluent to remove the side products followed by elution with dichloromethane/ethyl acetate to afford the title compound as a pale yellow oil (0.64 g).

Provenance & Evidence