Methyl 2-(bromomethyl)-3-phenylacrylate → (E)-2-Formyloxymethyl-3-phenylacrylic acid methyl ester

HRID 1071578Notes

Reaction equation

HRID 1071578 reaction equation
[CH:1]([O-:3])=[O:2].C([NH+](CC)CC)C.[CH3:11][O:12][C:13](=[O:24])/[C:14](/[CH2:22]Br)=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH3:11][O:12][C:13](=[O:24])/[C:14](/[CH2:22][O:3][CH:1]=[O:2])=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 5904127Methyl 2-(bromomethyl)-3-phenylacrylateHCID 10219518Triethylazanium;formate

Product 1

HCID 86759761(E)-2-Formyloxymethyl-3-phenylacrylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of triethylammonium formate (1.87 g) in acetonitrile (4 ml) was added (Z)-2-bromomethyl-3-phenylacrylic acid methyl ester (1.30 g) and the mixture heated at reflux for 2 hours. The reaction was cooled and extracted into diethyl ether (3×10 ml). The combined organics were dried (MgSO4) and concentrated under reduced pressure to afford the title compound as a crude oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction was cooled
  4. extractionextracted into diethyl ether (3×10 ml)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7d56f59ddeb45fbaac69457384e656a
Source dataset
uspto-grants-2005_06
Patent number
US06906085B2

Reaction notes

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