Diketene → trans-4,4,4-Trifluoro-2-buten-1-yl acetoacetate

Participants

Reaction Steps

To a refluxing solution of 4,4,4-trifluoro-2-buten-1-ol (10 g, 79 mmol) and sodium acetate (0.51 g, 6.2 mmol) in anhydrous tetrahydrofuran (27 mL) under nitrogen, a solution of diketene (6.7 mL, 43.1 mmol) in anhydrous tetrahydrofuran (14 mL) was added dropwise over a period of 1 hour. The reaction mixture was heated at reflux for an additional 30 min upon completion of the addition. Then, the reaction mixture mixture was cooled to room temperature and diluted with diethyl ether (100 mL). The resulting solution was washed with a saturated aqueous sodium chloride solution (2×20 mL) and the organic layer was dried over sodium sulfate, filtered and the solvent removed under reduced pressure. The brown residue was purified by column chromatography using a mixture 4:1 of hexane and ethyl acetate as eluent to afford 14.0 g (84% yield) of trans-4,4,4-trifluoro-2-buten-1-yl acetoacetate as a colorless liquid.

Provenance & Evidence