Potassium Carbonate → Methyl 2-(methoxymethyl)prop-2-enoate

HRID 1038017Notes

Reaction equation

HRID 1038017 reaction equation
Br[CH2:2][C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5].[C:9](=O)([O-])[O-:10].[K+].[K+].C[O-].[Na+]>CO>[CH3:9][O:10][CH2:2][C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5210932-Propenoic acid, 2-(bromomethyl)-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 10887940Methyl 2-(methoxymethyl)prop-2-enoateYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of methyl 2-(bromomethyl)acrylate (239 μl, 2 mmol) in petroleum ether (3 ml) was added potassium carbonate (276 mg, 2 mmol), followed by sodium methoxide (119 mg, 2.2 mmol) and methanol (450 μl). The resulting mixture was stirred overnight, filtered, concentrated to a residue that was purified by column chromatography eluting with 10% ether in hexanes to provide the title compound (150 mg, 58%). (Reference: J. Med. Chem.; 42; 15; 1999; 2760-2773.)

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to a residue that
  3. customwas purified by column chromatography
  4. washeluting with 10% ether in hexanes

Sources & evidence

ORD record
ord-ed3f2d28c6c3422a980631674c423cc1
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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