Triacetoxyperiodinane → 1-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-2-(3-methoxy-phenyl)-ethanone

HRID 2101486Notes

Reaction equation

HRID 2101486 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH:11]([OH:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11](=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 578015241-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-2-(3-methoxy-phenyl)-ethanol

Product 1

HCID 119514231-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-2-(3-methoxy-phenyl)-ethanoneYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-2-(3-methoxy-phenyl)-ethanol (40 mg, 0.11 mmol) in CH2Cl2 (1 mL) at 0° C. was added Dess-Martin periodinane (54 mg, 0.13 mmol). The mixture was stirred at ambient temperature for 2 h and then purified directly by column chromatography (silica gel, 8:1 to 4:1 hexane/EtOAc) to provide the title compound (19 mg, 48%) as an off-white solid: ESI MS m/z 375 [C19H16Cl2N2O2+H]+.

Workup

  1. custompurified directly by column chromatography (silica gel, 8:1 to 4:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-5c0341fff8264d1bab77681722a5f3c8
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

Loading…