Imidazole → 3,5-Dimethoxybenzyl tert-butyldiphenylsilyl ether

HRID 24705

Reaktionsgleichung

Reaktionsgleichung von HRID 24705
[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>>[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

Komponenten

4

Edukt 3

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

Produkt 1

HCID 225718833,5-Dimethoxybenzyl tert-butyldiphenylsilyl etherAusbeute 87,9 %

Versuchsvorschrift

A mixture of 3,5-dimethoxybenzyl alcohol (4.0 g), t-butyl-diphenylsilyl chloride (6.54 g) and imidazole (3.28 g) in DML (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+).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4b8ebf0f858447abb7f17f0abe7bc319
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855843B2

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