Imidazole → HCID 11391116, compound

HRID 2177047Notes

Reaction equation

HRID 2177047 reaction equation
[C:1]1([CH:7]([OH:10])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>ClCCl>[Si:11]([O:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:10])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

5

Reactant 3

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

Product 1

HCID 11391116HCID 11391116, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) and stirred solution of 1-phenylethane-1,2-diol (1.0 g, 7.24 mmol) and tert-butyldimethylsilyl chloride (1.1 g, 7.24 mmol) in dichloromethane was added imidazole (0.74 g, 10.86 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 20 hours. The reaction mixture was washed with water, dried, and concentrated to yield 1.8 g of 2-(tert-butyldimethylsilanyloxy)-1-phenylethanol.

Workup

  1. temperatureThe reaction mixture was slowly warmed to room temperature
  2. washThe reaction mixture was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-764039ffac994cc1a23e77f7ba38a673
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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