Ethyl Propionate → 2-[3,4-Bis(methyloxy)phenyl]-3-oxopentanenitrile

To a mixture of [3,4-bis(methyloxy)phenyl]acetonitrile (2.0 g, 11 mmol) and ethyl propanoate (1.61 mL, 14 mmol) in ethanol (4 mL) was added a sodium ethoxide solution (21%, 8.4 mL, 23 mmol), and the resulting mixture was heated at reflux for 18 hours. After cooling to room temperature, it was poured into a mixture of ice-water (50 mL). This aqueous mixture was washed with dichloromethane (3×20 mL) then acidified to pH 1. The acidified mixture was extracted with ethyl acetate (3×30 mL). The combined extract was washed with saturated sodium bicarbonate solution, brine, dried over sodium sulfate, filtered and concentrated to give 2-[3,4-bis(methyloxy)phenyl]-3-oxopentanenitrile as a brown oil (0.8 g, 3.4 mmol, 30% yield), MS (EI) for C13H15NO3: 234 (MH+).

1. temperaturethe resulting mixture was heated
2. temperatureat reflux for 18 hours
3. washThis aqueous mixture was washed with dichloromethane (3×20 mL)
4. extractionThe acidified mixture was extracted with ethyl acetate (3×30 mL)
5. extractionThe combined extract
6. washwas washed with saturated sodium bicarbonate solution, brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORDレコード

ord-15e60d3e86dc43cab4711d354105fed8

出典データセット

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07872014B2