Reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:14][C:15]#[N:16].[C:17](OCC)(=[O:19])[CH3:18]>O1CCCC1>[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:14]([C:17](=[O:19])[CH3:18])[C:15]#[N:16]Participants
Conditions
- Temperature
- 60 °C
Procedure
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+).
Workup
- temperatureThen it was cooled to room temperature
- washThis aqueous mixture was washed with dichloromethane (3×20 mL)
- extractionThe acidified mixture was extracted with ethyl acetate (3×30 mL)
- extractionThe combined extract
- washwas washed with saturated sodium bicarbonate solution, brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-da9d490d4547482eb84ed54e8e9d2e64
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872014B2
Linked notes
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