Sodium Hydroxide → HCID 86746208, compound

Participants

Reaction Steps

To a solution of 5.0 g (14.3 mmol) of 5-(cyanomethyl)-4-(2-methylpropyl-2-(difluoromethyl)-6-(trifluoromethyl)-3-pyridinecarboxylic acid, methyl ester, prepared as in Example d, above, 5.0 g (34.9 mmol) 1-methyl-4-chlorobutyryl chloride, 0.37 g benzyltriethylammonium chloride, and 150 mL dichloromethane was added 82 mL 50% NaOH. The solution was stirred at room temperature for 2 hours. The reaction was then quenched with ice water and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered through silica gel and concentrated to give 5.2 g of crude product. Purification by chromatography using 20% ethyl acetate in hexanes yielded 3.1 g of the desired product as a yellow oil, a 51% yield. nD25 1.4887.

Provenance & Evidence