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 1268874

Reaktionsgleichung

Reaktionsgleichung von HRID 1268874
[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

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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 4 Å 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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-917d3f7ca82f4d328e9a5b0fd13eb57b
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199119B2

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