Tetrahydrofuran → HCID 6150793, compound

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.

1. additionadded dropwise over a period of 1 hour
2. temperatureThe reaction mixture was heated
3. temperatureat reflux for an additional 30 min upon completion of the addition
4. washThe resulting solution was washed with a saturated aqueous sodium chloride
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customthe solvent removed under reduced pressure
8. customThe brown residue was purified by column chromatography

ORD record

ord-367a0b3de16a430c9c3ef3aedd09331d

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06504052B1