N-bromobutanimide → Ethyl 5-ethyl-2-methylfuran-3-carboxylate

HRID 2398652Notes

Reaction equation

HRID 2398652 reaction equation
[C:1]([C:4](=[CH:10][CH2:11][CH2:12][CH3:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH2:12]([C:11]1[O:3][C:1]([CH3:2])=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:10]=1)[CH3:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 348796HCID 348796, compound

Product 1

HCID 12448862Ethyl 5-ethyl-2-methylfuran-3-carboxylateYield 91.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3.69 g (0.02 mole) ethyl 2-acetyl-2-hexenoate and 3.56 g (0.02 mole) N-bromosuccinimide in 50 ml of carbon tetrachloride was heated at reflux for 4 hours. After cooling, the succinimide was removed by filtration and the solution concentrated in vacuo. Distillation of the crude product gave 3.32 g (91%) of ethyl 5-ethyl-2-methyl-3-furoate, bp 99°-101° C. (10 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureAfter cooling
  4. customthe succinimide was removed by filtration
  5. concentrationthe solution concentrated in vacuo
  6. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-86cc1db51d3c4d2b96cc10b93a9a16f5
Source dataset
uspto-grants-1977_05
Patent number
US04025537

Reaction notes

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