Sodium Hydroxide → HCID 131717578, compound

Participants

Reaction Steps

A 250-mL round-bottom flask equipped with a mechanical stirrer was charged with 2.0 g (5.7 mmol) 5-(cyanomethyl)-4-(2-methylpropyl)-2-(difluoromethyl)-6-(trifluoromethyl)-3-pyridinecarboxylic acid, methyl ester, prepared as in Example d, above, 95 mL dichloromethane, 0.12 g of benzyltriethylammonium chloride, and 2.4 g (11.3 mmol) of 2,2-dimethyl-4-bromobutyryl chloride. The solution was stirred and 24 mL 50% NaOH was added. Two additional equivalents of acid chloride were added after 15 minutes. No further progress of the reaction was noted so the solution was quenched by pouring into water and extracted with ethyl ether. The organics were washed with water, filtered, and concentrated to give 3.1 g of the desired product as a crude light brown oil. Purification by chromatography using 18% ethyl acetate in hexanes yielded 200 mg of the desired product as an oil, an 8% yield. nD25 1.4840.

Provenance & Evidence