Imidazole → 3,5-Dimethoxybenzyl tert-butyldiphenylsilyl ether

HRID 1060481

Reaction equation

HRID 1060481 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>[Si:13]([O:7][CH2:6][C:5]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:3]([O:2][CH3:1])[CH:4]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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), tert-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-dimethoxybenzyl tert-butyldiphenylsilyl ether. 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-fab6cf9405ac44258e70faa458d6f91c
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Linked notes

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