Dimethylformamide → 2-Vinylbenzofuran

HRID 374014Notes

Reaction equation

HRID 374014 reaction equation
CN(C)[CH:3]=[O:4].O1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[C:7]1[CH:15]=O.[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+]>CCCCCC>[CH:13]([C:12]1[O:4][C:3]2[CH:15]=[CH:7][CH:8]=[CH:9][C:10]=2[CH:11]=1)=[CH2:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 613412-BenzofurancarboxaldehydeHCID 638159Methyltriphenylphosphonium iodide

Product 1

HCID 5889742-VinylbenzofuranYield 25%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 20 ml of N,N-dimethylformamide were added 1.60 g of 2-benzofurancarbaldehyde and 4.90 g of methyltriphenylphosphonium iodide. Thereto was added 0.50 g of 60% sodium hydride with stirring under ice cooling. The mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 100 ml of n-hexane. The resulting mixture was washed with water and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: n-hexane) to obtain 0.40 g (yield: 25%) of 2-vinylbenzofuran as a colorless oily material.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. washThe resulting mixture was washed with water
  3. dry with materialan aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography (eluant: n-hexane)

Sources & evidence

ORD record
ord-b9e5e1ef8f2c45c28ccc2e88a11217b6
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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