Imidazole → 3,5-Dimethoxybenzyl tert-butyldiphenylsilyl ether

HRID 1060478

Reaction equation

HRID 1060478 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH2:6][OH:7].[Si:13](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CN=C1>CN(C=O)C>[CH3:12][O:11][C:9]1[CH:8]=[C:5]([CH2:6][O:7][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 697183,5-Dimethoxybenzyl alcoholHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 225718833,5-Dimethoxybenzyl tert-butyldiphenylsilyl etherYield 87.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,5-dimethoxybenzyl alcohol (4.0 g), t-butyl-diphenylsilyl chloride (6.54 g) and imidazole (3.28 g) in DMF (60 mL) was stirred at room temperature for 24 h. DMF was evaporated and the residue was purified by column chromatography (silica gel; eluent: hexane to hexane/EtOAc 20%) to yield 8.5 g of 3,5-dimethoxy-1-[(t-butyldiphenylsilyloxy)methyl]benzene. ESMS: m/z 407 (MH+).

Workup

  1. customDMF was evaporated
  2. customthe residue was purified by column chromatography (silica gel; eluent: hexane to hexane/EtOAc 20%)

Sources & evidence

ORD record
ord-4841f5c4415d4c9b8f8776b2224e030b
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Linked notes

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