Imidazole → 3-(Tert-butyldiphenylsiloxy)propanol

HRID 1517629Notes

Reaction equation

HRID 1517629 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].N1C=CN=C1.[Si:11](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O.C(OCC)(=O)C>[Si:11]([O:4][CH2:3][CH2:2][CH2:1][OH:5])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 104421,3-PropanediolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 102451343-(Tert-butyldiphenylsiloxy)propanol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,3-propanediol (1.25 g, 16.4 mmol) in N,N-dimethylformamide (50 mL) was added imidazole (2.23 g, 32.8 mmol) and tert-butyldiphenylsilyl chloride (4.97 g, 18.1 mmol). The reaction was stirred for 3 days at room temperature, then was diluted with ethyl acetate and was washed with water and brine. Concentration in vacuo afforded the crude product as a thick colorless oil which was used directly in the next step.

Workup

  1. washwas washed with water and brine
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-2a60f97ccc6e46e8bb3ffdba69a0f81d
Source dataset
uspto-grants-2012_07
Patent number
US08232309B2

Reaction notes

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