Acetonitrile → HCID 57440379, compound

Reaction equation

[C:1](#[N:3])[CH3:2].[H-].[Na+].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][C:16](OC)=[O:17])[CH:11]=[CH:12][CH:13]=1>O1CCOCC1>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][C:16](=[O:17])[CH2:2][C:1]#[N:3])[CH:11]=[CH:12][CH:13]=1

Participants

Procedure

Acetonitrile (3.36 ml, 64.25 mmol, 1 eq) was added to a slurry of sodium hydride (2.57 g dispersion in mineral oil, 64.25 mmol, 1 eq) in anhydrous 1,4-dioxane (50 ml) and the mixture was stirred at room temperature for 20 mins. Methyl 3-(3-methoxyphenyl)propanoate (10.4 g, 53.54 mmol, 1 eq) in 1,4-dioxane (25 ml) was added and the reaction was refluxed for 2 h. The reaction mixture was cooled and quenched with water. The residue was dissolved in 2M HCl and extracted into ethyl acetate. The organic layer was separated, washed with 2M HCl, water and brine and dried over magnesium sulphate. Evaporation under reduced pressure gave yield to a yellow oil, which was purified by silica column chromatography, eluting with a mixture of 0-50% ethyl acetate in hexanes. Fractions containing the product were combined and evaporated to leave 5-(3-methoxyphenyl)-3-oxo-pentanenitrile (5.37 g, 49% yield).