Acetonitrile → HCID 66583168, compound

Temperature

-78 °C

CH3CN (2.55 mL, 48.8 mmol. 2.2 eq) was added dropwise to a solution of nBuLi (48.8 mmol) in 180 mL of THF at −78° C. After stirring for 1 h at −78° C., a solution of ethyl 4-methylenecyclohexanecarboxylate (3.73 g, 22.2 mmol) in 20 mL of THF was added dropwise and the resulting reaction mixture (turned into nearly clear solution after addition) was stirred at −78° C. for 1 h, then slowly warmed to 0° C. before being quenched with sat. NH4Cl. THF was removed and the residue was diluted with EtOAc. The organic layer was separated and washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by a SiO2 column (0-30% EtOAc/Hexanes, Rf=0.2 in 20% EtOAc) to afford 3-(4-methylenecyclohexyl)-3-oxopropanenitrile as a colorless oil (3.25 g, 90%).

1. customthe resulting reaction mixture (
2. additionafter addition)
3. stirringwas stirred at −78° C. for 1 h
4. temperatureslowly warmed to 0° C.
5. custombefore being quenched with sat. NH4Cl
6. customTHF was removed
7. additionthe residue was diluted with EtOAc
8. customThe organic layer was separated
9. washwashed with brine
10. dry with materialdried over Na2SO4
11. concentrationconcentrated
12. customThe crude product was purified by a SiO2 column (0-30% EtOAc/Hexanes, Rf=0.2 in 20% EtOAc)

ORD record

ord-57b3a15509d84ef0a143827ce2178a84

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703784B2