Dichloromethane → 3-Acetoxy-2-{1-(methoxycarbonyl)ethoxy}pyridine
Reaction equation
B(F)(F)F.[CH3:5][CH2:6][O:7][CH2:8][CH3:9].NC1[C:12]([O:17][CH:18]([C:20]([O:22][CH3:23])=[O:21])[CH3:19])=[N:13][CH:14]=[CH:15]C=1.ClCCl.N(OC(C)(C)C)=[O:28]>COCCOC.C(OC(=O)C)(=O)C.CCCCC>[C:6]([O:7][C:8]1[C:12]([O:17][CH:18]([C:20]([O:22][CH3:23])=[O:21])[CH3:19])=[N:13][CH:14]=[CH:15][CH:9]=1)(=[O:28])[CH3:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 70 °C
Procedure
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.
Workup
- additionAfter mixing for 10 minutes at the same temperature
- additionwas poured into the mixture
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-a7c2dd07015746ffb6d393ca7dbb9d4f
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06537948B1
Reaction notes
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