6-(BENZYLOXY)NICOTINALDEHYDE

83664-33-9

68-12-2

635712-99-1

General procedure for the synthesis of 6-(benzyloxy)nicotinaldehyde from 2-benzyloxy-5-bromopyridine and N,N-dimethylformamide: n-butyllithium (2.5 M hexane solution, 2.61 mL, 1.05 eq.) was slowly added to a tetrahydrofuran solution (25 mL, -78 °C) of 2-benzyloxy-5-bromopyridine (1.64 g, 6.2 mmol). After 1 hour of reaction at -78 °C, N,N-dimethylformamide (0.97 mL, 2 eq.) was added and stirring was continued at -78 °C for 30 minutes. The reaction mixture was rapidly poured into a stirring 5% aqueous sodium bicarbonate solution (50 mL) and extracted with ether (3 x 50 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give a crude product of 1.16 g (quantitative yield), which could be used in the next reaction without further purification. Mass spectrometry analysis showed a molecular ion peak of 186.34 ([MH]+) for the target compound.