Aluminium lithium hydride → 2-Methyl-6-(trifluoromethyl)nicotinaldehyde

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To a cooled (−78° C.) solution of N-methoxy-N-methyl-2-methyl-6-trifluoromethyl-3-pyridinecarboxamide (615 mg, 2.48 mmol) in THF (10 mL) was added lithium aluminum hydride (LAH, 1 N/THF, 1.23 mL). The mixture was stirred for 15 minutes, and then warmed to −10° C. After additional stirring for 30 minutes, the mixture was quenched with saturated potassium hydrogen sulfate solution (1 mL) and extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 2-methyl-6-trifluoromethyl-3-pyridinecarboxaldehyde quantitatively as oil. The crude product was used directly in the following reaction.

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