Tetrahydrofuran → HCID 6150793, compound

Participants

Reaction Steps

To a refluxing solution of crotyl alcohol (21.5 mL, 252 mmol) and sodium acetate (1.24 g, 15.12mmol) in anhydrous tetrahydrofuran (70 mL) under nitrogen, a solution of diketene (21.34 mL, 277.1 mmol) in anhydrous tetrahydrofuran (30 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 was cooled to room temperature and diluted with diethyl ether (300 mL). The resulting solution was washed with a saturated aqueous sodium chloride. solution (2×50 mL) and organic layer. dried over sodium sulfate, filtered and the solvent removed under reduced pressure. The brown residue was purified by column chromatography using a mixture 5:1 of hexane and diethyl ether as eluent to afford 33.0 g (83% yield) of trans-2-buten-1-yl acetoacetate as a colorless liquid.

Provenance & Evidence