Tetrahydrofuran → 1,1,1-Trifluoro-2-(trifluoromethyl)but-3-en-2-ol

To 1.6 M vinylmagnesium chloride in THF (200 mL, 0.32 mol) at −78° C. was added hexafluoroacetone (50 g, 0.31 mol) by cannula over a period of 3 h with stirring. The reaction mixture was allowed to warm to r.t. and stirred for an additional 2 h, then heated to 40° C. for an additional 1 h. The reaction mixture was quenched with aqueous NH4Cl solution. The mixture was diluted with pentane, filtered, and the organic phase was dried over MgSO4. Fractional distillation (12 inch Vigreux column) at 100-103° C. afforded the product 1,1,1-trifluoro-2-trifluoromethyl-but-3-en-2-ol (mixture containing around 66 mol % THF) as a clear liquid (50 g). 1H NMR δ 5.20 (br, 1H), 5.70 (d, 1H), 5.92 (m, 2H).

1. stirringstirred for an additional 2 h
2. temperatureheated to 40° C. for an additional 1 h
3. customThe reaction mixture was quenched with aqueous NH4Cl solution
4. additionThe mixture was diluted with pentane
5. filtrationfiltered
6. dry with materialthe organic phase was dried over MgSO4
7. distillationFractional distillation (12 inch Vigreux column) at 100-103° C.

ORD record

ord-094f7ce9c54f407596d3c79aadd08883

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524969B2