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

HRID 2267399노트

반응식

HRID 2267399 반응식
[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

참가 물질

6

반응물 3

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

생성물 2

HCID 9015411-(3-Phenylthiophen-2-yl)ethanone수율 41%HCID 135416931-(4-Phenylthiophen-2-yl)ethan-1-one수율 29%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.)

후처리

  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

출처 및 근거

ORD 기록
ord-82af840b72f44d509b0062b7fd75c206
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858785B2

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