3-Hydroxybenzaldehyde → 3-(t-Butyldimethylsilyloxy)benzaldehyde

HRID 644567Notes

Reaction equation

HRID 644567 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14].N1C=CN=C1>>[Si:5]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7]

Participants

4

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 112071113-(t-Butyldimethylsilyloxy)benzaldehyde

Procedure

In a manner analogous to example 1 g, by reaction of 42.7 g (0.275 mol) of tert-butyldimethylchlorosilane with 30.5 g (0.2 mol) of 3-hydroxybenzaldehyde and (20.4 g, 0.3 mol) of imidazole. After purification on a silica column (dichloromethane 20-heptane 80), a yellow oil is obtained (m=55.9 g; Y=95%).

Workup

  1. customAfter purification on a silica column (dichloromethane 20-heptane 80)
  2. customa yellow oil is obtained (m=55.9 g; Y=95%)

Sources & evidence

ORD record
ord-e2eaf4bc612e4ac2ab13360e0fba7500
Source dataset
uspto-grants-2010_04
Patent number
US07700657B2

Reaction notes

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