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

HRID 2266141ノート

反応式

HRID 2266141 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a601fd35eab04c98aa847269ac7905e5
出典データセット
uspto-grants-2010_12
特許番号
US07858632B2

反応ノート

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