Acetyl chloride → 1-[4-Isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-phenyl]ethanone

HRID 2266141노트

반응식

HRID 2266141 반응식
[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])([CH3:3])[CH3:2].[C:22](Cl)(=[O:24])[CH3:23].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[CH:1]([C:4]1[C:5]([S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:13])=[O:14])=[CH:6][C:7]([C:22](=[O:24])[CH3:23])=[C:8]([O:10][CH3:11])[CH:9]=1)([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 670535032-Isopropyl-4-methoxy-1-(toluene-4-sulfonyl)-benzene

생성물 1

HCID 670534431-[4-Isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-phenyl]ethanone수율 81.9%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a clear solution of 2-Isopropyl4-methoxy-1-(toluene-4-sulfonyl)-benzene (5.3 g, 16.56 mmol) in DCE (50 ml) was added acetyl chloride (2.0 g, 24.84 mmol) and AlCl3 (3.3 g, 24.84 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hrs and quenched by H2O (10 ml). Ten minutes after quenching, the aqueous solution was extracted into CH2Cl2. The combined extracts was washed with H2O, dried wover Na2SO4, filtered and concentrated. Flashed chromatography on silica gel (0 to 30% EtOAc in Hex) gave 1-[4-Isopropyl-2-methoxy-5-(toluene4-sulfonyl)-phenyl]-ethanone (4.7 g, 79%) as white solid.

후처리

  1. customquenched by H2O (10 ml)
  2. customTen minutes after quenching
  3. extractionthe aqueous solution was extracted into CH2Cl2
  4. washThe combined extracts was washed with H2O
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a601fd35eab04c98aa847269ac7905e5
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858632B2

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