Trityl chloride → [1-(triphenylmethyl)-1H-imidazol-4-yl]methanol

HRID 1274075Notes

Reaction equation

HRID 1274075 reaction equation
C(N(C(C)C)CC)(C)C.[NH:10]1[CH:14]=[C:13]([CH2:15][OH:16])[N:12]=[CH:11]1.[C:17]1([C:23](Cl)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC#N>[C:17]1([C:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:10]2[CH:14]=[C:13]([CH2:15][OH:16])[N:12]=[CH:11]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 178519868HCID 178519868, compound

Product 1

HCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanolYield 82.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diisopropylethylamine (14 mL, 80 mmol) was added dropwise to a suspension of 4-imidazole methanol (5.4 g, 40 mmol) in CH3CN (15 mL) at 0° C. A homogeneous yellow solution was formed. To this solution was added triphenylmethyl chloride (11.2 g, 40 mmol). The reaction mixture was stirred at room temperature for 2 h. The resultant white precipitate was filtered and washed successively with saturated NaHCO3 aqueous solution (2×20 mL) and water (2×20 mL), then dried in a vacuum oven (45° C.) for 12 h to afford a white solid 11.2 g (82%) which was used in next step without further purification.

Workup

  1. customA homogeneous yellow solution was formed
  2. filtrationThe resultant white precipitate was filtered
  3. washwashed successively with saturated NaHCO3 aqueous solution (2×20 mL) and water (2×20 mL)
  4. customdried in a vacuum oven (45° C.) for 12 h

Sources & evidence

ORD record
ord-397216c9a0894548895890bc7da0dfe8
Source dataset
uspto-grants-2000_12
Patent number
US06156746

Reaction notes

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