Acetyl chloride → 1-(3-Phenylthiophen-2-yl)ethanone

HRID 2267399ノート

反応式

HRID 2267399 の反応式
[C:1]1([C:7]2[CH:11]=[CH:10][S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](Cl)(=[O:14])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[C:1]1([C:7]2[CH:11]=[CH:10][S:9][C:8]=2[C:12](=[O:14])[CH3:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([C:7]2[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[S:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 6367Acetyl chlorideHCID 754733-PhenylthiopheneHCID 6451240Aluminum(III) Chloride

生成物 2

HCID 9015411-(3-Phenylthiophen-2-yl)ethanone収率 41%HCID 135416931-(4-Phenylthiophen-2-yl)ethan-1-one収率 29%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 3-phenylthiophene (3.10 g, 19.3 mmol) and acetyl chloride (1.38 mL, 23.2 mmol) in dichloromethane (50 mL) was cooled to 0° C. Aluminium (III) chloride (2.58 g, 19.3 mmol) was added in several portions to control an otherwise vigorous exotherm. After addition was complete, the bath was removed and the reaction allowed to stir at ambient temperature for 2 h. The reaction mixture was then diluted with saturated aqueous NaHCO3 and the layers were separated. The organic phase was washed with another portion of NaHCO3 solution and brine. The resulting dichloromethane solution was concentrated in vacuo and the residue was purified by flash chromatography eluting with a gradient of 1-5% EtOAc/hexanes to afford 1.62 g (41% yield) of 1-(3-phenylthiophen-2-yl)ethanone and 1.13 g (29% yield) of 1-(4-phenylthiophen-2-yl)ethanone which were both spectroscpopically identical to literature compounds (See reference: Acta Chemica Scandinavica (1947-1973) 1970, 24, pp. 99-104.)

後処理

  1. additionAfter addition
  2. customthe bath was removed
  3. additionThe reaction mixture was then diluted with saturated aqueous NaHCO3
  4. customthe layers were separated
  5. washThe organic phase was washed with another portion of NaHCO3 solution and brine
  6. concentrationThe resulting dichloromethane solution was concentrated in vacuo
  7. customthe residue was purified by flash chromatography
  8. washeluting with a gradient of 1-5% EtOAc/hexanes

出典と根拠

ORDレコード
ord-82af840b72f44d509b0062b7fd75c206
出典データセット
uspto-grants-2010_12
特許番号
US07858785B2

反応ノート

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