2-(Bromomethyl)acrylic acid ethyl ester → Ethyl 2-(methoxymethyl)prop-2-enoate

HRID 729441Notes

Reaction equation

HRID 729441 reaction equation
Br[CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:10][O-:11].[Na+]>CO.O>[CH2:7]([O:6][C:4](=[O:5])[C:3]([CH2:2][O:11][CH3:10])=[CH2:9])[CH3:8]

Participants

5

Reactant 2

HCID 3106202-(Bromomethyl)acrylic acid ethyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 20770134Ethyl 2-(methoxymethyl)prop-2-enoateYield 28.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of ethyl α-(bromomethyl)acrylate (0.99 g, 5.1 mmol [Villieras J., Rambaud M., Synthesis, 1982:924-926]) in methanol (10 mL) is added to an ice-cold solution of sodium methoxide (0.33 g, 6.1 mmol) in methanol (50 mL). The suspension is refluxed for 21 hours, cooled, diluted with water and extracted with dichloromethane. The organic extracts are dried over Na2SO4, filtered and concentrated under vacuum. The resulting residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes) to afford the title compound (0.211 g). 1H NMR (200 MHz, CDCl3): δ 6.33-6.26 (m, 1H), 5.88-5.80 (m, 1H), 4.23 (q, 2H), 4.19-4.10 (m, 2H), 3.41 (s, 311), 1.31 (t, 3H).

Workup

  1. temperatureThe suspension is refluxed for 21 hours
  2. temperaturecooled
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic extracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe resulting residue is purified by flash column chromatography (1:5 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2878eb458ef34ba6a77771ed4785578b
Source dataset
uspto-grants-2009_09
Patent number
US07582627B2

Reaction notes

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