Ethyl Acetate → 2-(3,4-Bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile

Temperature

60 °C

To a suspension of (3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile (0.59 g, 2.2 mmol), and sodium hydride (40% oil dispersion, 270 mg, 6.7 mmol) in tetrahydrofuran (10 mL), was added ethyl acetate (1.1 mL, 11.1 mmol), and the resulting mixture was stirred at 60° C. for 1.5 hours. Then it was cooled to room temperature, and poured into a mixture of ice-water (50 mL). This aqueous mixture was washed with dichloromethane (3×20 mL) then acidified to pH of 2. 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{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile (0.57 g, 1.9 mmol, 86% yield), MS (EI) for C16H21NO5: 308 (MH+).

1. temperatureThen it was cooled to room temperature
2. washThis aqueous mixture was washed with dichloromethane (3×20 mL)
3. extractionThe acidified mixture was extracted with ethyl acetate (3×30 mL)
4. extractionThe combined extract
5. washwas washed with saturated sodium bicarbonate solution, brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-a6c19d6caeb249298a51aeef550cfa9d

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872014B2