Imidazole → HCID 11391116, compound

HRID 1364469Notes

Reaction equation

HRID 1364469 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-44b8dde966ec42caaed58997931514a5
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

Loading…