Allyl bromide → Methyl 5-(prop-2-enyloxy)benzofuran-2-carboxylate

HRID 2295421Notes

Reaction equation

HRID 2295421 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][C:6]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>CC(C)=O>[CH2:23]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][C:6]=2[CH:14]=1)[CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 12208973Methyl 5-hydroxybenzofuran-2-carboxylate

Product 1

HCID 20282933Methyl 5-(prop-2-enyloxy)benzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 5-hydroxybenzofuran-2-carboxylate (4.14 g), potassium carbonate (5.95 g) and allyl bromide (3.73 ml) in dry acetone (100 ml) was refluxed and stirred for 16 hours. The solvent was evaporated and the residue was partitioned between water and ether. The ether was washed with water, dried and evaporated to give methyl 5-(prop-2-enyloxy)benzofuran-2-carboxylate (4.7 g) as a solid, characterised by NMR and mass spectral data. This ester (3.74 g) in N-methylpyrrolidinone (30 ml) was refluxed under nitrogen for 2 hr, cooled, and partitioned between water and ethyl acetate. The organic phase was washed with water, dried and evaporated to give the title ester (3.5 g), mp 114°-119°.

Workup

  1. temperaturewas refluxed
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water and ether
  4. washThe ether was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-c7893167993043df88793d5567e4ffaf
Source dataset
uspto-grants-1984_01
Patent number
US04424231

Reaction notes

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