(2,3-Dimethylphenyl)(1-trityl-1H-imidazol-5-yl)methanone → (2,3-dimethylphenyl)(phenyl)(1-trityl-1H-imidazol-5-yl)methanol

HRID 1516608Notes

Reaction equation

HRID 1516608 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[N:15]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[N:13][CH:12]=1)=[O:10].[C:35]1([Mg]Br)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:11]1[N:15]([C:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:14]=[N:13][CH:12]=1)[OH:10]

Participants

4

Reactant 2

HCID 42631463(2,3-Dimethylphenyl)(1-trityl-1H-imidazol-5-yl)methanoneHCID 178418255HCID 178418255, compound

Product 1

HCID 58238336(2,3-dimethylphenyl)(phenyl)(1-trityl-1H-imidazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2,3-dimethylphenyl)(1-trityl-1H-imidazol-5-yl)methanone, (Intermediate 3) (1.2 g, 2.7 mmol) in dichloromethane (30 mL) was treated with phenyl-magnesium bromide (1.35 mL, 4.05 mmol, 3 M in THF) 0° C. and then stirred for 16 h at rt. The mixture was quenched with water (10 mL) and a saturated solution of ammonium chloride (10 mL). The residue was isolated in a typical aqueous workup to give (2,3-dimethylphenyl)(phenyl)(1-trityl-1H-imidazol-5-yl)methanol, (Intermediate 4), (crude).

Workup

  1. customThe mixture was quenched with water (10 mL)
  2. customThe residue was isolated in a typical aqueous workup

Sources & evidence

ORD record
ord-eade2456e4d54f7a9b1679504b078f20
Source dataset
uspto-grants-2012_07
Patent number
US08227499B2

Reaction notes

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