Reaction #65256

Reaction equation

ether hexane

sodium hydride

Ethyl 3-ketoheptanoate

N-phenyltrifluoro-methanesulfonamide

→

ethyl 3-trifluoromethanesulfonyloxy-2-heptenoate

Solvents

ether water

dimethylformamide

Conditions

Procedure

Ethyl 3-ketoheptanoate (2.07 g, 12 mmol) was dissolved in dimethylformamide (60 mL) under argon and sodium hydride (357 mg, 14.4 mmol) was added. After 30 minutes at room temperature the solid N-phenyltrifluoro-methanesulfonamide (Tetra. Letters, (1983), 24, 979) (4.97 g, 13.8 mmol) was added. The reaction was stirred for 2 hours, diluted with ether/water and the usual workup gave after chromatography with 5:95 ether/hexane 3.45 g (94%) of ethyl 3-trifluoromethanesulfonyloxy-2-heptenoate.

Source