Acetonitrile → 3-Cyclobutyl-3-oxopropanenitrile

Temperature

75 °C

A stirred suspension of sodium hydride (12 g of a 60% dispersion in mineral oil, 0.30 mol, which was washed with petroleum ether twice in dry THF) was heated to 75° C. To this was added a mixture of ethyl cyclobutanecarboxylate (25.64 g, 0.20 mol) and dry acetonitrile (12.32 g, 0.30 mol), dropwise, and the resulting colorless suspension was heated at 70° C. for 24 h. After cooling to rt the reaction mixture was concentrated under reduced pressure and the residue poured into water (100 mL) and extracted with ethyl acetate (100 mL). The aqueous layer was separated, acidified to pH 2 with aqueous 2 M HCl and extracted with diethyl ether (2×200 mL). The combined diethyl ether layers were dried over magnesium sulfate then concentrated under reduced pressure to afford 3-cyclobutyl-3-oxopropanenitrile as yellow oil which was used in the next step without further purification.

1. washwas washed with petroleum ether twice in dry THF)
2. additionTo this was added
3. temperaturedropwise, and the resulting colorless suspension was heated at 70° C. for 24 h
4. temperatureAfter cooling to rt the reaction mixture
5. concentrationwas concentrated under reduced pressure
6. additionthe residue poured into water (100 mL)
7. extractionextracted with ethyl acetate (100 mL)
8. customThe aqueous layer was separated
9. extractionextracted with diethyl ether (2×200 mL)
10. dry with materialThe combined diethyl ether layers were dried over magnesium sulfate
11. concentrationthen concentrated under reduced pressure

ORD record

ord-df4d756f0f134696b67c2ed1e1c0fa1b

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618289B2