Dichloromethane → 3-Acetoxy-2-(methoxycarbonyl)methoxypyridine

0.41 g of trifluoromethanesulfonic acid was added to a mixture of 0.5 g of 3-amino-2-(methoxycarbonyl)methoxypyridine, 1.5 ml of 1,2-dimethoxyethane and 0.5 ml of dichloromethane dropwise at −5° C. The mixture was stirred for 10 minutes at the same temperature, then, a solution of 0.34 g of t-butyl nitrite in 0.5 ml of 1,2-dimethoxyethane was added to the reaction solution dropwise at −5° C. or lower. The mixture was stirred for 1 hour at the same temperature, then, n-pentane was poured into the mixture. The lower layer of two separated layers was dissolved in 1.5 ml of acetic anhydride, and the mixture was stirred for 30 minutes at 60° C. The reaction solution was cooled to room temperature, then, poured into water, and extracted with t-butyl methyl ether. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated saline, then, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel chromatography to obtain 0.30 g of 3-acetoxy-2-(methoxycarbonyl)methoxypyridine.

1. stirringThe mixture was stirred for 1 hour at the same temperature
2. stirringthe mixture was stirred for 30 minutes at 60° C
3. extractionextracted with t-butyl methyl ether
4. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated saline
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated

ORD record

ord-2790a2f2cc7f4a4a896df64aa06d979a

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06537948B1