Trityl chloride → (5-Methyl-1-trityl-1H-imidazol-4-yl)methanol

HRID 1382776Notes

Reaction equation

HRID 1382776 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:22][C:23]1[N:24]=[CH:25][NH:26][C:27]=1[CH2:28][OH:29].C(N(CC)CC)C>CN(C=O)C>[CH3:22][C:23]1[N:24]([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:25]=[N:26][C:27]=1[CH2:28][OH:29]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178433279HCID 178433279, compound

Product 1

HCID 11544901(5-Methyl-1-trityl-1H-imidazol-4-yl)methanolYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of triphenylchloromethane (13.1 g) in dry DMF (80 ml) was added dropwise over 0.5 h to a stirred solution of 4-methyl-5-imidazolemethanol hydrochloride (7.0 g) and triethylamine (9.52 g) in dry DMF (75 ml) at room temperature under nitrogen, and stirring was continued for 2.5 h. The suspension was poured onto ice (600 ml), stirred for 0.5 h and filtered to give a solid (12.0 g). This solid was triturated twice with acetone (2×250 ml) to give the title compound (8.4 g) as a white solid, t.l.c. (System A 94.5:5:0.5), Rf 0.19.

Workup

  1. additionThe suspension was poured onto ice (600 ml)
  2. stirringstirred for 0.5 h
  3. filtrationfiltered

Sources & evidence

ORD record
ord-178eb51372e14488b0e111f8998b80f7
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

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