Imidazole → HCID 11391116, compound

HRID 1075644Notes

Reaction equation

HRID 1075644 reaction equation
[C:1]1([CH:7]([OH:10])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CN=C1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.C(OCC)(=O)C>[Si:20]([O:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:10])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 71491-Phenyl-1,2-ethanediolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11391116HCID 11391116, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1-phenyl-1,2-ethanediol (1.38 g, 10 mmole), immidazole (817 mg, 12 mmole), and tert-butylchlorodimethylsilane (1.81 g, 12 mmole) in DMF 15 (ml) was stirred at 0° C. for 1.5 hrs and then at room temperature overnight. The resulting mixture was diluted with ethyl acetate, washed with water, brine, and dried over sodium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (1:4) as eluent. 2-(tert-butyidimethylsilyl)oxy-1-phenylethanol was obtained as an oil (2.6 g, 100% yield).

Workup

  1. customat room temperature
  2. customovernight
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of the solvent
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d647c0dad44240ebb7076f1b58eec5d4
Source dataset
uspto-grants-1999_05
Patent number
US05905076

Reaction notes

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