Trifluoroacetic acid → 5-(Phenyl-o-tolyl-methyl)-1H-imidazole

HRID 1516610Notes

Reaction equation

HRID 1516610 reaction equation
[C:1]1([C:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])([C:9]2[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:11]=[N:12][CH:13]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>ClCCl>[C:1]1([CH:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[C:9]2[NH:10][CH:11]=[N:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052TriethylsilaneHCID 67103477phenyl-o-tolyl-(3-trityl-3H-imidazol-4-yl)-methanol

Product 1

HCID 441992045-(Phenyl-o-tolyl-methyl)-1H-imidazoleYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenyl-o-tolyl-(3-trityl-3H-imidazol-4-yl)-methanol, (Intermediate 8) (620 g, 1.2 mmol) in dichloromethane (30 mL) was reacted with TFA: trifluoroacetic acid (4.0 ml) and triethylsilane (TES) (6.0 ml) at rt for 24 h. The mixture was evaporated under reduced pressure and quenched with solid NaHCO3. This material was subjected to an aqueous work-up and the residue was purified by chromatography on silica gel with 5% NH3-MeOH:CH2Cl2 to yield 5-(Phenyl-o-tolyl-methyl)-1H-imidazole 162 mg (53%). 1HNMR (CD3OD, 300 MHz) δ 7.8 (s, 1H), 7.12-7.38 (m, 9H), 6.82 (s, 1H), 6.40 (s, 1H), 5.60 (s, 1H), 2.21 (s, 1H).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customquenched with solid NaHCO3
  3. customthe residue was purified by chromatography on silica gel with 5% NH3-MeOH

Sources & evidence

ORD record
ord-3603ef447e444c17bfd21f5944758f5a
Source dataset
uspto-grants-2012_07
Patent number
US08227499B2

Reaction notes

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