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

HRID 81812노트

반응식

HRID 81812 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-Isopropyl-4-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 over Na2SO4, filtered and concentrated. Flashed chromatography on silica gel (0 to 30% EtOAc in Hex) gave 1-[4-Isopropyl-2-methoxy-5-(toluene-4-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. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3e3be2178f394c08a91f0b9d8ff43e07
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846705B2

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