1-(4-Chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanol → 1-(4-Chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanone

HRID 1868327

反応式

HRID 1868327 の反応式
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:6]=2[C:5]([CH:17]([OH:19])[CH3:18])=[CH:4][N:3]=1>ClCCl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:6]=2[C:5]([C:17](=[O:19])[CH3:18])=[CH:4][N:3]=1

参加物

4

反応物 1

HCID 184465111-(4-Chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanol

生成物 1

HCID 184465121-(4-Chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanone

試薬・触媒・溶媒 2

HCID 178419074HCID 178419074、化合物触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 1-(4-chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanol 96 (92 mg, 0.32 mmol) and 168 mg of powdered 4A molecular sieves in dichloromethane (35 mL) was added TPAP (11 mg, 0.03 mmol). The resultant mixture was stirred at room temperature for 1 h. After this time, the reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium thiosulfate (1×) and saturated aqueous copper sulfate (1×). The organic layer was dried over Na2SO4, filtered, and the filtrate was purified by silica gel column chromatography (eluent: hexane:EtOAc, 17:3) to give 97. 1H NMR (400 MHz, CDCl3) δ: 2.79 (s, 3H), 7.40-7.53 (m, 3H), 7.75 (s, 1H), 7.78-7.83 (m, 2H), 8.83 (s, 1H). MS (EI) m/z (M+H+) 288.

後処理

  1. washwashed with saturated aqueous sodium thiosulfate (1×) and saturated aqueous copper sulfate (1×)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe filtrate was purified by silica gel column chromatography (eluent: hexane:EtOAc, 17:3)

出典と根拠

ORDレコード
ord-b0eafc1a48e74bdeb0e02867d7465f17
出典データセット
uspto-grants-2009_12
特許番号
US07635695B2

関連ノート

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