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

HRID 1516609Notes

Reaction equation

HRID 1516609 reaction equation
C1([C:7]2[C:8]([C:14]([C:16]3[N:17]([C:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:18]=[N:19][CH:20]=3)=[O:15])=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)C=CC=CC=1.[C:40]1(C)[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[Mg]Br.Cl[CH2:50]Cl>>[C:40]1([C:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH3:50])([C:16]2[N:17]([C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:18]=[N:19][CH:20]=2)[OH:15])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[CH3:13][C:9]1[C:10]([CH3:50])=[CH:11][CH:12]=[CH:7][C:8]=1[C:14]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:16]1[N:17]([C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:18]=[N:19][CH:20]=1)[OH:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67103996phenyl-o-tolyl-(3-trityl-3H-imidazol-4-yl)-methanoneHCID 178424303HCID 178424303, compound

Product 2

HCID 58238336(2,3-dimethylphenyl)(phenyl)(1-trityl-1H-imidazol-5-yl)methanolHCID 67103477phenyl-o-tolyl-(3-trityl-3H-imidazol-4-yl)-methanol

Procedure

A solution of phenyl-o-tolyl-(3-trityl-3H-imidazol-4-yl)-methanone (500 mg, 1.2 mmol) in dichloromethane (25 mL) at rt was treated with o-tolyl magnesium bromide (1.2 mL, 2.4 mmol, 2M in ether) and the reaction mixture was then stirred at rt for 16 h. The mixture was quenched with water (50 mL) and a sat. solution of ammonium chloride (20 mL). The residue was isolated in a typical aqueous to give phenyl-o-tolyl-(3-trityl-3H-imidazol-4-yl)-methanol, (Intermediate 4) (620 mg, crude).

Workup

  1. customThe mixture was quenched with water (50 mL)
  2. customThe residue was isolated in a typical aqueous

Sources & evidence

ORD record
ord-1020e531cc8c443e981799cde3158384
Source dataset
uspto-grants-2012_07
Patent number
US08227499B2

Reaction notes

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