Benzoyl chloride → HCID 57826353, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of sodium cyanide (1.96 g, 40 mmol) and benzyltridimethylammonium chloride (0.3 g, 1.3 mmol) in 7.5 mL of water was slowly added a solution of 3-pyridinecarboxaldehyde (0.88 mL, 9.3 mmol) in 15 mL of methylene chloride at 0° C. The resulting reaction solution was stirred at 0° C. for 15 min, and then benzoyl chloride (1.16 mL, 10 mmol) was additionally added thereto. After addition was complete, the reaction solution was elevated to room temperature and further stirred for 3 hours. After the reaction was complete, the reaction materials was diluted with 50 mL of ethyl acetate and 50 mL of water to dissolve salts, followed by separation of layers. The obtained organic layer was successively washed twice with 50 mL of a brine solution. The organic layer was dried over magnesium sulfate, filtered, concentrated under reduced pressure and purified by silica gel column chromatography, to give 1.95 g (yield: 95%) of benzoic acid cyano-pyridin-3-yl-methyl ester of the following formula.

Provenance & Evidence