反应详情

温度

75 °C

In a round bottomed flask flushed with argon, a suspension of sodium hydride 60% in mineral oil (1.30 g, 34 mmoles) was rinsed twice with hexane, and suspended in 20 mL of dry THF. The solution was heated to 75° C., and ethyl difluoropropionate (3.00 g, 22 mmoles) and acetonitrile (1.78 mL) in 5 ml of dry THF was added dropwise over 30 minutes. The temperature of the reaction was lowered to 65° C. and stirred overnight. The mixture was then concentrated to an oil and partitioned between water and ether, and extracted twice to remove any mineral oil and other impurities. The aqueous layer was acidified to pH=1 with 10% HCl, and the solution extracted twice. These extracts were dried over magnesium sulfate, filtered and concentrated to a crude oil. The crude product was purified using silica gel chromatography using a gradient of 10-40% ethyl acetate/hexane to afford 4,4-difluoro-3-oxo-pentanenitrile 1H (300 MHz, CDCl3) δ 3.95 (s, 2H), 1.86 (m, 3H).

1. customIn a round bottomed flask flushed with argon
2. washwas rinsed twice with hexane
3. customwas lowered to 65° C.
4. concentrationThe mixture was then concentrated to an oil
5. custompartitioned between water and ether
6. extractionextracted twice
7. customto remove any mineral oil and other impurities
8. extractionthe solution extracted twice
9. dry with materialThese extracts were dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated to a crude oil
12. customThe crude product was purified