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

HRID 2104367Notes

Reaction equation

HRID 2104367 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][O:5][C:6](=[O:11])[C:7]([CH2:9]Br)=[CH2:8].[CH3:12][OH:13]>C(OCC)C>[CH3:4][O:5][C:6](=[O:11])[CH:7]([CH2:9][O:13][CH3:12])[CH2:8][O:2][CH3:1]

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 2-(bromomethyl)acrylic acid methyl ester (1.0 mL) in methanol (10 mL), and the mixture was heated under reflux for 26 hours. The reaction mixture was cooled, and was diluted with diethyl ether. The precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate hexane=1:4), to thereby give the title compound (726 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 26 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe precipitate was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate hexane=1:4)

Sources & evidence

ORD record
ord-16046a5f93d547d2b4805e75044ddccc
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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