Water → HCID 20513506, compound

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:17][C:18]#N.[H-].[Na+].[CH3:22]I.O.C[N:26]([CH3:29])C=O>>[CH3:1][O:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:7][CH:6]=[CH:5][C:4]=1[C:17]([CH3:18])([CH3:22])[C:29]#[N:26]

Participants

Reactant 5

HCID 962Water

HCID 6228Dimethylformamide2×

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 20513415HCID 20513415, compound

Product 1

HCID 20513506HCID 20513506, compound

Procedure

A solution of 2-[2-methoxy-3-(o-tolyloxy)phenyl]acetonitrile (5.2 g) in dimethylformamide (10 ml) was added dropwise to a mixture of 50% sodium hydride (1.1 g) and dimethylformamide (20 ml) below 7° C. in 10 minutes and stirred at the same temperature for 30 minutes. Methyl iodide (6.2 g) was added dropwise to the mixture below 7° C. in 15 minutes and stirred at the same temperature for an hour. Chilled water (200 ml) was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with water, aqueous sodium hydrogen sulfite and water successively, dried over magnesium sulfate and then evaporated to give oily 2-[2-methoxy-3-(o-tolyloxy)phenyl]-2,2-dimethylacetonitrile (5.7 g).