Dichloromethane → 3-Acetoxy-2-{1-(methoxycarbonyl)ethoxy}pyridine

Participants

Reaction Conditions

Reaction Steps

1.5 ml of boron trifluoride diethyl etherate was added to a mixture of 1.1 g of 3-amino-2-{1-(methoxycarbonyl)ethoxy}pyridine, 3 ml of 1,2-dimethoxyethane and 1 ml of dichloromethane dropwise at −10° C. After mixing for 10 minutes at the same temperature, a solution of 0.80 ml of t-butyl nitrite in 1 ml of 1,2-dimethoxyethane was added to the reaction solution dropwise at −5° C. or lower. After mixing for 30 minutes at the same temperature, n-pentane was poured into the mixture. The lower layer of two separated layers was dissolved in 5 ml of acetic anhydride, and the mixture was stirred for 1 hour at 70° C. The solvent was distilled off, then, the resulted residue was subjected to silica gel chromatography to obtain 0.34 g of 3-acetoxy-2-{1-(methoxycarbonyl)ethoxy}pyridine.

Provenance & Evidence