Acetyl chloride → Methyl 5-acetylbenzofuran-2-carboxylate

HRID 864779

반응식

HRID 864779 반응식
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)=[O:4].[C:14](Cl)(=[O:16])[CH3:15].[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[C:14]([C:11]1[CH:12]=[CH:13][C:7]2[O:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:9][C:8]=2[CH:10]=1)(=[O:16])[CH3:15]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 291153Methyl 1-benzofuran-2-carboxylateHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 18918314Methyl 5-acetylbenzofuran-2-carboxylate

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매

실험 절차

To a solution of 2-benzofuranoic acid methyl ester in carbon disulphide (240 ml) cooled to 5° C. was added acetyl chloride (70 ml) followed portionwise over 1 hour by aluminium trichloride (40 g). The mixture was heated under reflux for 42 hours before cooling and decanting the carbon disulphide. The residual complex was destroyed by the addition of iced water (50 ml) and 2N HCl (50 ml). The resulting mixture was extracted with ethyl acetate (3×200 ml). The organic layers were combined, washed with water (100 ml), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography, eluting with ethyl acetate / hexane (10:90 to 40:60, v/v), to give methyl 5-acetylbenzofuran-2-carboxylate as a solid (3.099 g); NMR 2.68 (3H,s), 4.00(3H,s), 7.6-8.35(4H,m).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 42 hours
  3. temperaturebefore cooling
  4. customdecanting the carbon disulphide
  5. customThe residual complex was destroyed by the addition of iced water (50 ml) and 2N HCl (50 ml)
  6. extractionThe resulting mixture was extracted with ethyl acetate (3×200 ml)
  7. washwashed with water (100 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was purified by flash column chromatography
  11. washeluting with ethyl acetate / hexane (10:90 to 40:60

출처 및 근거

ORD 기록
ord-6987bc4d3aff4655b3cd6f2228d59476
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563141

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