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

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).

1. filtrationThe mixture was filtered through celite after 21.5 hours
2. washwashing with dichloromethane
3. concentrationconcentrated
4. additiondiluted with toluene (20 ml)
5. washwashed with saturated aqueous sodium chloride (2×20 ml)
6. dry with materialdried (Na2SO4)
7. customevaporated
8. customto give a light yellow oil
9. customThe yellow oil was purified by chromatography over silica using
10. additiona 1:1 mixture of dichloromethane/cyclohexane as eluent
11. customto remove the side products
12. washfollowed by elution with dichloromethane/ethyl acetate

ORD record

ord-4ecfce6892bc4e899d1b805d8981a8ba

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247377B2