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

Reaction equation

HRID 1868327 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b0eafc1a48e74bdeb0e02867d7465f17
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Linked notes

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