Dichloromethane → 3-Acetoxy-2-(methoxycarbonyl)methoxypyridine
Reaction equation
N[C:2]1[C:3]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:4][CH:5]=[CH:6][CH:7]=1.ClCCl.N([O:19][C:20]([CH3:23])(C)C)=O.CCCCC.C[O:30]CCOC>>[C:20]([O:19][C:2]1[C:3]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:30])[CH3:23]Participants
Procedure
First, 1.6 g of a boron trifluoride diethyl ether complex was added dropwise to a mixture of 1.0 g of 3-amino-2-(methoxycarbonyl)methoxypyridine, 3 ml of 1,2-dimethoxyethane, and 1 ml of dichloromethane at −10° C. After stirring at the same temperature for 10 minutes, a solution of 0.68 g of t-butyl nitrite in 1 ml of 1,2-dimethoxyethane was added dropwise to the reaction mixture at −5° C. or lower. After stirring at the same temperature for 30 minutes, n-pentane was poured into the mixture. The lower one of the two layers separated was dissolved in 5 ml of acetic anhydride, and the solution was stirred at 80° C. for 1 hour. After the solvent was distilled out, the residue was subjected to silica gel chromatography to give 0.45 g of 3-acetoxy-2-(methoxycarbonyl)methoxypyridine.
Workup
- stirringAfter stirring at the same temperature for 30 minutes
- customThe lower one of the two layers separated
- dissolutionwas dissolved in 5 ml of acetic anhydride
- stirringthe solution was stirred at 80° C. for 1 hour
- distillationAfter the solvent was distilled out
Sources & evidence
- ORD record
- ord-299595b510fb4e97a24a7533d359e2b0
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109148B2
Reaction notes
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