Imidazole → (3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanol

HRID 1761031Notes

Reaction equation

HRID 1761031 reaction equation
[C:1]1([CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.N1C=CN=C1.[Cl-].[C:17]([SiH:21]([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O.CCOCC>[Si:21]([O:8][CH2:7][C:3]1[CH:2]=[C:1]([CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 693741,3-BenzenedimethanolHCID 131722836Tert-butyldimethylsilane chloride

Product 1

HCID 10658493(3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1,3-benzenedimethanol (2 g; 14.47 mmol) in 50 ml of dimethylformamide is stirred at ambient temperature. Imidazole (1.97 g; 28.94 mmol) and tert-butyl(dimethyl)silane chloride (2.18 g; 14.47 mmol) are added in succession. After stirring for 12 hours, the reaction mixture is diluted with ether and washed with a saturated aqueous sodium chloride solution. After extraction, the ethereal phase is dried over magnesium sulphate and concentrated to yield the expected compound.

Workup

  1. washwashed with a saturated aqueous sodium chloride solution
  2. extractionAfter extraction
  3. dry with materialthe ethereal phase is dried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-065e9b157ea041828e862cc530d70eb9
Source dataset
uspto-grants-2005_01
Patent number
US06846833B2

Reaction notes

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