Methanol → Methyl 3-methoxy-2-(methoxymethyl)propanoate

HRID 1392744Notes

Reaction equation

HRID 1392744 reaction equation
[CH3:1][O-:2].[Na+].Br[CH2:5][C:6](=[CH2:11])[C:7]([O:9][CH3:10])=[O:8].[CH3:12][OH:13]>C(OCC)C>[CH3:1][O:2][CH2:5][CH:6]([CH2:11][O:13][CH3:12])[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 5210932-Propenoic acid, 2-(bromomethyl)-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 22934772Methyl 3-methoxy-2-(methoxymethyl)propanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium methoxide (1.21 g) was added to a solution of methyl 2-(bromomethyl)acrylate (1.0 ml) in methanol (10 ml), and the mixture was heated under reflux for 26 hours. After cooling, the reaction mixture was diluted with diethyl ether, and precipitate was collected by filtration and the filtrate was concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound (726 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 26 hours
  3. temperatureAfter cooling
  4. filtrationwas collected by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-61a4ad58fd024dc1af01e08dffb50109
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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