4-(Benzyloxy)-3-methoxybenzaldehyde → Methyl-2-azido-3-[4'-(benzyloxy)-3'-methoxyphenyl]prop-2-enoate

Participants

Reaction Conditions

Reaction Steps

A solution of the 4-Benzyloxy-3-methoxy-benzaldehyde (12.0 g, 49.6 mmol) and methyl azidoacetate (23 g, 0.200 mol) in methanol (50 mL) was added over 30 min to a cooled (ice-salt bath) solution of sodium methoxide which had been prepared from addition of methanol (80 mL) to sodium (3.4 g, 0.149 mol). The reaction mixture was stirred at 0° C. for 45 min, during this time a thick cream precipitate formed, and then stood in the freezer overnight. Ice-cold water was added and the precipitate was removed by filtration and dried to give methyl-2-azido-3-[4′-(benzyloxy)-3′-methoxyphenyl]prop-2-enoate (55) (12.2 g, 73%) which was used in the next step without purification.

Provenance & Evidence