Tetrahydro-4H-pyran-4-one → 4-Ethynyloxan-4-ol

Temperature

25 °C

A solution of tetrahydro-4H-pyran-4-one (1.25 g, 12.5 mmol) in tetrahydrofuran (10 mL) was cooled to 0° C. and then treated with a 0.5M solution of ethylene magnesium bromide in tetrahydrofuran (40 mL, 20 mmol). The mixture was stirred at 0° C. for 2 h and at 25° C. for 4 h. The resulting mixture was cooled to 0° C. and then diluted with methanol (10 ml). The solvents were concentrated in vacuo, and the residue was extracted with a saturated aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was dried in vacuo to afford solid 4-ethynyl-tetrahydro-pyran-4-ol (1.2 g, 95.2%).

1. temperatureThe resulting mixture was cooled to 0° C.
2. concentrationThe solvents were concentrated in vacuo
3. extractionthe residue was extracted with a saturated aqueous ammonium chloride solution and ethyl acetate
4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was dried in vacuo

ORD record

ord-7fd09454723c4282931baf34e592860c

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07132425B2