Triethylamine → HCID 57966308, compound

Participants

Reaction Steps

To a mixture of 3-(methoxymethoxy)-4-methylbenzyl alcohol described in WO2004/022551 (9.80 g; 53.78 mmol), triethylamine (7.90 ml; 56.47 mmol) and anhydrous THF (50 ml) was added dropwise methanesulfonyl chloride (4.40 ml; 56.47 mmol) under ice-cooling. The mixture was stirred at the same temperature for 1.5 hours. The precipitate was collected and condensed under reduced pressure. Then, to the residue were added sodium cyanide (7.91 g; 0.161 mol) and anhydrous N,N-dimethylformamide (50 ml). The mixture was stirred at room temperature for 3 days. Water and ethyl acetate were added to the reaction solution. The organic layer was separated, washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=3:1) to give [3-(methoxymethoxy)-4-methylphenyl]acetonitrile as blackish brown oil (7.87 g; 77%).

Provenance & Evidence