Dimethylformamide dimethyl acetal → HCID 71114823, compound

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Reaction Steps

4-(4,4-Dimethyl-3-oxo-cyclohexyl)-3-methyl-benzonitrile (0.6 g, 2.49 mmol) in N,N-dimethylformamide dimethylacetal (50 mL) is stirred at 90° C. for two days. The mixture is cooled to room temperature and concentrated in vacuo. The residue is diluted with ethyl acetate (50 mL) and water (50 mL). The organic phase is separated and the aqueous phase is extracted with ethyl acetate (3×50 mL). The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by silica gel flash chromatography, eluting with pet ether:EtOAc 1:1 to MeOH:DCM=1:30 to give 4-[(2Z)-2-(dimethylaminomethylene)-4,4-dimethyl-3-oxo-cyclohexyl]-3-methyl-benzonitrile (0.2 g, 27%).

Provenance & Evidence