Thiophene → 4-(Thiophen-2-yl)benzaldehyde

HRID 1277004

反応式

HRID 1277004 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[S:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.C([O-])(=O)C.[K+]>CC(N(C)C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 8030ThiopheneHCID 707414-BromobenzaldehydeHCID 517044Potassium Acetate

生成物 1

HCID 7364994-(Thiophen-2-yl)benzaldehyde

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

3.7 g (20 mmol) of 4-bromobenzaldehyde, 9.5 ml (120 mmol) of thiophene, 2.94 g (30 mmol) of potassium acetate and 1.16 g (1 mmol) of tetrakis(triphenylphosphine)palladium (Fluka, Buchs, Switzerland) in 50 ml of dimethylacetamide are placed in a pressure reactor and stirred at 150° C. under nitrogen for 16 hours. The reaction mixture is concentrated by evaporation; the residue is taken up in water and extracted three times with methylene chloride. After removal of the solvent, the residue is chromatographed on silica gel (hexane/ethyl acetate 4:1). The title compound is obtained in the form of a yellow solid. TLC: Rf =0.36 (hexane/ethyl acetate 4:1). HPLC20-100 : tRet =15.26. 1H-NMR (CD3OD; 200 MHz): 9.98/s (1H); 7.93 and 7.85/each d, J=9.5 (2×2H); 7.60/d, J=2.5 (1H); 7.52/d, J=5 (1H); 7.171dxd, J=2.5 and 5 (1H).

後処理

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. extractionextracted three times with methylene chloride
  3. customAfter removal of the solvent
  4. customthe residue is chromatographed on silica gel (hexane/ethyl acetate 4:1)

出典と根拠

ORDレコード
ord-716a42c32dcb4313a12d7a216b4bbe11
出典データセット
uspto-grants-2000_12
特許番号
US06166004

関連ノート

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