Dichloromethane → HCID 18619220, compound

HRID 1862292Notes

Reaction equation

HRID 1862292 reaction equation
B(F)(F)F.[CH3:5][CH2:6][O:7][CH2:8][CH3:9].NC1[C:12]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[N:13][C:14]([O:17][CH3:18])=[CH:15]C=1.ClCCl.N(OC(C)(C)C)=[O:29]>COCCOC.C(OC(=O)C)(=O)C.CCCCC>[C:6]([O:7][C:8]1[C:12]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:9]=1)(=[O:29])[CH3:5]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 10906Tert-Butyl nitriteHCID 18619201HCID 18619201, compound

Product 1

HCID 18619220HCID 18619220, compound

Reagents, catalysts & solvents 3

HCID 7918Acetic AnhydrideSolventHCID 8003PentaneSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

A boron trifluoride diethyl etherate is added to a mixture of 3-amino-6-methoxy-2-(methoxycarbonyl)methoxypyridine, 1,2-dimethoxyethane and dichloromethane dropwise at −10° C. After mixing for 10 minutes at the same temperature, a solution of t-butyl nitrite in 1,2-dimethoxyethane is added to the reaction solution dropwise at −5° C. or lower. After mixing for 30 minutes at the same temperature, n-pentane is poured into the mixture. The lower layer of two separated layers is dissolved in acetic anhydride, and the mixture is stirred for 1 hour at 80° C. The solvent is distilled off, then, the resulted residue is subjected to silica gel chromatography to obtain 3-acetoxy-6-methoxy-2-(methoxycarbonyl)methoxypyridine.

Workup

  1. additionAfter mixing for 10 minutes at the same temperature
  2. additionis poured into the mixture
  3. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-36b591b2c776418e89897f73efbfe3ec
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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