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

HRID 27695

반응식

HRID 27695 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5958b8bb344240e6b41ec79d9aaa4f9a
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04223035

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