Acetonitrile → 3-Cyclobutyl-3-oxopropanenitrile

To 390 mL of THF at −78° C. was added n-BuLi (312 mL, 780 mmol, 2.5 M in hexanes). After the reaction temperature equilibrated (˜15 min), a solution of acetonitrile (40.7 mL, 780.0 mmol in 200 mL of THF) was added dropwise via an addition funnel over a 20 min period. The resulting milky-white slurry was allowed to stir for 1 hr before a solution of ethyl cyclobutane carboxalate (50.0 g, 390.1 mmol in 100 mL of THF) was added down the inside of the flask over a 15 min period. After 1 hr, the reaction was warmed to −45° C. (acetonitrile/CO2) and allowed to stir for 2 hr. The reaction was quenched cold by the dropwise addition of 2 N HCl (pH=7) and then diluted with EtOAc. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound (quantitative yield) as a colorless oil that was used without further purification. LRMS m/z (APCl) 121 (M−1).

1. custom(˜15 min)
2. additionwas added down the inside of the flask over a 15 min period
3. customThe reaction was quenched cold by the dropwise addition of 2 N HCl (pH=7)
4. additiondiluted with EtOAc
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with CH2Cl2
7. dry with materialThe combined organic layers were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-9209e17ef9a74dd2ba31c57d38f2511e

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07300943B2