2-Benzofurancarboxaldehyde → 2-Vinylbenzofuran

HRID 1459660Notes

Reaction equation

HRID 1459660 reaction equation
[CH3:1]C(C)([O-])C.[K+].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]1[CH:16]=O>O1CCCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O>[CH:16]([C:8]1[O:7][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=1)=[CH2:1]

Participants

6

Reactant 2

HCID 613412-BenzofurancarboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 5889742-Vinylbenzofuran

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

92 ml of a 1N solution of potassium tert-butoxide in tetrahydrofuran are added dropwise to a vigorously stirred mixture at 0° C. of 68.4 mmol of benzofuran-2-carboxaldehyde and 92 mmol of methyltriphenylphosphonium bromide in 200 ml of tetrahydrofuran and 150 ml of dimethylformamide. The medium is stirred for 2 h at room temperature, poured into 2 liters of ice-water and extracted with ether. After concentration of the solvents, the residue is taken up in 1 liter of petroleum ether and the precipitate is filtered off and washed with petroleum ether. The expected product is obtained by evaporation of the filtrate.

Workup

  1. extractionextracted with ether
  2. filtrationthe precipitate is filtered off
  3. washwashed with petroleum ether

Sources & evidence

ORD record
ord-abc4f898b19744728300d93751798b6c
Source dataset
uspto-grants-1998_12
Patent number
US05854273

Reaction notes

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