Sodium Hydroxide → HCID 22250820, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methyl-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester (200 mg, 0.5 mmol) in diethyl ether (3 ml) was added to a suspension of lithium aluminium hydride (40 mg, 1 mmol) in diethyl ether (6 ml) under an argon atmosphere at ambient temperature within 5 min. The mixture was stirred at reflux for 12 h, cooled to 0° C. and treated cautiously with ice water (6 ml) and 10% aqueous NaOH (3 ml). The reaction mixture was filtered over celite, t-butyl methylether was added and the layers were separated. The aqueous layer was extracted one more time with t-butyl methylether, the combined organic layers were washed with ice water/brine 1/1 and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a brown oil which was purified by column chromatography (silica gel, heptane/AcOEt) to yield 80 mg (240 μmol, 45%) of the title compound as yellow crystals.

Provenance & Evidence