2-Acetylthiophene → 2-[2-(2-Thienyl)-1-propenyl]benzonitrile

HRID 27695

Reaction equation

HRID 27695 reaction equation
C([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)(=O)C.C([C:11]([CH2:24][CH3:25])(P(=O)([O-])[O-])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[N:19])C.C[O-].[Na+]>CN(C)C=O>[S:5]1[CH:6]=[CH:7][CH:8]=[C:4]1[C:24]([CH3:25])=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[N:19]

Participants

5

Reactant 3

HCID 69202-AcetylthiopheneHCID 10942334Sodium MethoxideHCID 86737208Diethyl-o-cyanobenzylphosphonate

Product 1

HCID 540069522-[2-(2-Thienyl)-1-propenyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The starting material may be produced as follows: (a) A solution of 10.0 g of 2-acetylthiophene and 21.0 g of diethyl-o-cyanobenzylphosphonate in 70 cc of anhydrous dimethyl formamide is added dropwise at 20°-30° in an atmosphere of nitrogen to a suspension of 4.5 g of pulverized sodium methylate in 100 cc of anhydrous dimethyl formamide, the reaction mixture is stirred at 40° for 2 hours, and at 100° for a further 2 hours, is cooled to room temperature and diluted with 600 cc of ice water. The condensation product is extracted with ether, the extract is washed with water until neutral, is dried over potassium carbonate and concentrated by evaporation. The evaporation residue is chromatographed through 110 g of silica gel with a mixture of benzene/petroleum ether (1:4). The 2-[2-(2-thienyl)-1-propenyl]benzonitrile (nD20 =1.6460, B.P. 165°-175°/0.1 mm Hg), isolated as main fraction, is used for the next reaction without further purification.

Workup

  1. customThe starting material may be produced
  2. waitat 100° for a further 2 hours
  3. extractionThe condensation product is extracted with ether
  4. washthe extract is washed with water until neutral,
  5. dry with materialis dried over potassium carbonate
  6. concentrationconcentrated by evaporation
  7. customThe evaporation residue is chromatographed through 110 g of silica gel with a mixture of benzene/petroleum ether (1:4)

Sources & evidence

ORD record
ord-5958b8bb344240e6b41ec79d9aaa4f9a
Source dataset
uspto-grants-1980_09
Patent number
US04223035

Linked notes

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