Acrylonitrile → Diethyl (2-cyanoethyl)(3,4-difluorophenyl)propanedioate

HRID 71109Notes

Reaction equation

[O-]CC.[Na+].[F:5][C:6]1[CH:7]=[C:8]([CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[CH:10][C:11]=1[F:12].[C:24](#[N:27])[CH:25]=[CH2:26].[Cl-].[NH4+]>C(O)(C)(C)C>[C:24]([CH2:25][CH2:26][C:13]([C:8]1[CH:9]=[CH:10][C:11]([F:12])=[C:6]([F:5])[CH:7]=1)([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:27]

Participants

Conditions

Temperature: 40 °C

Procedure

Under an argon atmosphere, sodium ethoxide (20% ethanol solution, 1.7 g) was added to a mixture of diethyl (3,4-difluorophenyl)propanedioate (13.8 g) in tert-butylalcohol (50 mL) at room temperature, and the mixture was stirred at 40° C. for 30 min. Acrylonitrile (3.34 mL) was added to the reaction mixture at room temperature, and the mixture was stirred at room temperature overnight. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (15.2 g).

Workup

stirringthe mixture was stirred at room temperature overnight
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-4b125bf6e6384e3f9d5202abc9f5eb1a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822699B2

Reaction notes

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