Methyl iodide → HCID 67396424, compound

HRID 70505Notes

Reaction equation

HRID 70505 reaction equation
[CH3:1]I.[CH:3]1([C:6]2[CH:7]=[CH:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:10][C:11]=2[OH:12])[CH2:5][CH2:4]1>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[CH:3]1([C:6]2[CH:7]=[CH:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:10][C:11]=2[O:12][CH3:1])[CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178468719HCID 178468719, compound

Product 1

HCID 67396424HCID 67396424, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Silver carbonate (70 g) and methyl iodide (11.2 mL) were added to a solution of ethyl 5-cyclopropyl-6-hydroxypyridine-2-carboxylate (12.4 g) in chloroform (250 mL), and the mixture was stirred at 60° C. for eight hours. The reaction solution was filtered through celite, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1) to give ethyl 5-cyclopropyl-6-methoxypyridine-2-carboxylate (13.05 g, 99%) as a colorless oil.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-aa61374f8ec849648462943e19247edb
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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