Triethylamine → 1-(1-Acetoxymethyl-1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methyl-1-propanol

HRID 1368525

Reaction equation

HRID 1368525 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[CH:12]=2)([OH:10])[CH:7]([CH3:9])[CH3:8])[N:3]=[CH:2]1.[C:23]([O:26][CH2:27]Br)(=[O:25])[CH3:24].C(N(CC)CC)C>C1COCC1>[C:23]([O:26][CH2:27][N:1]1[CH:5]=[C:4]([C:6]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[CH:12]=2)([OH:10])[CH:7]([CH3:9])[CH3:8])[N:3]=[CH:2]1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68536Bromomethyl acetateHCID 178487492HCID 178487492, compound

Product 1

HCID 220184171-(1-Acetoxymethyl-1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methyl-1-propanolYield 24.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(1H-Imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methyl-1-propanol (100 mg) was dissolved in THF (6 ml), and to the solution were added bromomethyl acetate (160 mg) and triethylamine (40 mg). The mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated, and the residue was purified by silica gel chromatography (eluent, dichloromethane-methanol=20:1) to give the titled compound (30 mg) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel chromatography (eluent, dichloromethane-methanol=20:1)

Sources & evidence

ORD record
ord-7a39e942a0bc4c38ba41fc43aaec1887
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Linked notes

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