Dimethylformamide → HCID 17989247, compound

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#N)=[CH:4][C:3]=1[O:11][CH3:12].[CH3:13]I.[H-].[Na+].C[N:18]([CH3:21])C=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:9])[C:21]#[N:18])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 179892962-(4-Fluoro-3-methoxyphenyl)acetonitrile

Product 1

HCID 17989247HCID 17989247, compound

Procedure

16.67 g (100.93 mmol) of (4-fluoro-3-methoxyphenyl)-acetonitrile is introduced with 30.1 g (211.96 mmol) of methyliodide into 158 ml of dimethylformamide. At 0° C., 8.50 g (211.96 mmol) of a 55-60% sodium hydride suspension is added in portions. After stirring overnight at room temperature, the reaction mixture is poured into ice water and then extracted three times with methyl tert-butyl ether. The combined organic extracts are washed with water and with brine. After the solvent is dried and spun off, the residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 5.11 g (26.2%) of the desired compound and 6.18 g of the monomethyl compound, which is realkylated, are isolated.