Methanol → Methyl 4-(oxiran-2-yl)butanoate

HRID 638650Notes

Reaction equation

HRID 638650 reaction equation
Br[CH2:2][CH:3]1[O:7][C:6](=[O:8])[CH2:5][CH2:4]1.[CH3:9][O-:10].[Na+].[CH3:12]O>O>[CH3:12][O:7][C:6]([CH2:5][CH2:4][CH2:3][CH:2]1[O:10][CH2:9]1)=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 111377012(3H)-Furanone, 5-(bromomethyl)dihydro-

Product 1

HCID 13462612Methyl 4-(oxiran-2-yl)butanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.0 g 4,5-dihydro-5-bromomethyl-(3H)-furanone are refluxed with 3.0 g sodium methylate in 37 ml methanol for 5 hours. The solvent is eliminated in vacuum and the residue is dissolved in 20 ml H2O and then extracted with ether. The ethereal phase is dried through a molecular sieve and the ether eliminated in vacuum. The residue is distilled at 20 mm. 6.4 g 4,5-epoxypentane carboxylic acid methyl ester (boiling point at 20 mm, 85° C.) is obtained.

Workup

  1. extractionextracted with ether
  2. customThe ethereal phase is dried through a molecular sieve
  3. distillationThe residue is distilled at 20 mm

Sources & evidence

ORD record
ord-ec0153c58b604e3794c437fe8ec91fe3
Source dataset
uspto-grants-1985_12
Patent number
US04562270

Reaction notes

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