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

Temperature

60 °C

To a suspension of (2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile (0.17 g, 0.76 mmol) sodium hydride (40% oil dispersion, 93 mg, 2.3 mmol) in tetrahydrofuran (5 mL), was added ethyl acetate (0.37 mL, 0.38 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 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-(2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile (0.17 g, 0.65 mmol, 85% yield). MS (EI) for C14H17NO4: 264 (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-da9d490d4547482eb84ed54e8e9d2e64

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872014B2