Ethyl formate → 4-Methoxy-6-trifluoromethyl-pyrimidine-5-carbaldehyde

Participants

Reaction Steps

30.0 ml (48.0 mmol) of n-butyllithium (1.6 mol/l n-hexane solution) was slowly added to 100 ml of tetrahydrofuran solution containing 10.3 g (40.0 mmol) of 5-bromo-4-methoxy-6-trifluoromethylpyrimidine at −65 to −60° C., and the resultant mixture was stirred at 30 minutes. Further, 3.6 g (48.0 mmol) of ethyl formate was added thereto at the same temperature, and the mixture was stirred for 3 hours at the same temperature. The resultant reaction solution was poured into water and was extracted with ethyl acetate. The organic phase thus obtained was washed with water and an aqueous sodium chloride solution in this order, and then dried over anhydrous magnesium sulfate. The resultant solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography to obtain 1.3 g (yield: 15.8%) of 4-methoxy-6-trifluoromethylpyrimidine-5-carboaldehyde.

Provenance & Evidence