Dichloromethane → HCID 18619218, compound

1.46 ml of trifluoromethanesulfonic acid was added to a mixture of 3.0 g of 5-amino-2-(methoxycarbonyl)methoxypyridine, 9 ml of 1,2-dimethoxyethane and 3 ml of dichloromethane dropwise at −10° C. The mixture was stirred for 10 minutes at the same temperature, then, to the reaction solution was added a solution of 2.35 ml of t-butyl nitrite in 1 ml of 1,2-dimethoxyethane dropwise at −10° C. or lower. 1,2-dimethoxyethane was added to the mixture, and it was stirred for 20 minutes at the same temperature, then, into the mixture was poured n-pentane. The precipitated solid was washed with n-pentane, then it was dissolved in 18 ml of acetic anhydride, and the mixture was stirred for 2 hour at 80° C. The mixture was poured into ice-water, and extracted with t-butyl methyl ether. The organic layer was concentrated, then diluted with t-butyl methyl ether. The dilute was washed with saturated aqueous sodium bicarbonate solution, then saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue is subjected to silica gel column chromatography to obtain 1.4 g of 5-acetoxy-2-(methoxycarbonyl)methoxypyridine.

1. stirringwas stirred for 20 minutes at the same temperature
2. washThe precipitated solid was washed with n-pentane
3. dissolutionit was dissolved in 18 ml of acetic anhydride
4. stirringthe mixture was stirred for 2 hour at 80° C
5. additionThe mixture was poured into ice-water
6. extractionextracted with t-butyl methyl ether
7. concentrationThe organic layer was concentrated
8. additiondiluted with t-butyl methyl ether
9. washThe dilute was washed with saturated aqueous sodium bicarbonate solution
10. dry with materialsaturated saline, dried over anhydrous magnesium sulfate
11. concentrationconcentrated

ORD record

ord-50a7bf64fede49e4af87a096346ff57c

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06537948B1