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-e5c69b62f46b47b9adfe2fdd79b69f79

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119819B2