Ethyl Acetate → HCID 131717577, 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, 8.02 g 2-bromoethyl chloroformate, and 0.3 g benzyltriethylammonium chloride in 125 mL dichloromethane was added 82 mL 50% NaOH. The solution was stirred at room temperature for one hour. The mixture was then poured into ice water and extracted twice with ethyl ether. The organic layer was washed with brine, dried over magnesium sulfate, filtered through silica gel, and concentrated to give 3.2 g of crude dark yellow oil. Chromatography using 50% ethyl acetate in hexanes yielded 2.0 g of the desired product as a light yellow oil, a 56% yield, which crystallized upon standing. m.p. 121°-122° C.

Provenance & Evidence