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

HRID 977587

Reaction equation

HRID 977587 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][OH:15].N1C=CN=C1.S(=O)(=O)(O)O>CN(C)C=O.CCOCC>[Si:1]([O:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][OH:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 1118Sulfuric AcidHCID 28928tert-Butyldimethylsilyl chlorideHCID 693741,3-Benzenedimethanol

Product 1

HCID 10658493(3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanolYield 42.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

33.3 g of tert-butyldimethylsilyl chloride is added to a solution of 30 g of 3-hydroxymethylbenzyl alcohol and 30 g of imidazole in 250 ml of dimethylformamide at 0° C. under argon and stirred for. 20 hours at 25° C. It is diluted with 1.5 1 of ether, shaken twice with 100 ml of 10% sulfuric acid each, washed neutral with brine, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel. With hexane/0-80% ether, 23.4 g of 3-tert-butyldimethylsilyloxymethyl-benzyl alcohol is obtained as colorless oil.

Workup

  1. custom20 hours
  2. customat 25° C
  3. washwashed neutral with brine
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-e754f00fe4c64286bc920a8d5febe93e
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Linked notes

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