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

HRID 902851

Reaction equation

HRID 902851 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-2380bbf5a74c4fafaa8e79e6e211fbcd
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Linked notes

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