Acetonitrile → trans-3-Oxo-3-(2-phenylcyclopropyl)propanenitrile

Temperature

-60 °C

To a stirred solution of MeCN (208.3 mL) and THF (200 mL) at −60° C. under N2 was added dropwise 1M LHMDS in THF (1040 mL). The reaction mixture was stirred at −60° C. for 3 h, and 37 (62.5 g, 304.5 mmol, 1.00 equiv) was then added dropwise. The resulting solution was stirred at −60° C. for 10 min and then quenched with sat'd. aq. NH4Cl solution (400 mL). The reaction mixture was extracted with EtOAc (3×1 L), and the combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by SiO2 chromatography eluting with EtOAc/petroleum ether (10 to 25% EtOAc) to afford 28.5 g (51%) of trans-3-oxo-3-(2-phenylcyclopropyl)propanenitrile (39) as a light yellow oil.

1. stirringThe resulting solution was stirred at −60° C. for 10 min
2. customquenched with sat'd
3. extractionThe reaction mixture was extracted with EtOAc (3×1 L)
4. dry with materialthe combined organic layers were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude residue was purified by SiO2 chromatography
8. washeluting with EtOAc/petroleum ether (10 to 25% EtOAc)

ORD record

ord-d279c744cb8f44eebe6a5a45ad2ade41

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637537B2