Imidazole → 1-[(Tert-butyldimethylsilyl)oxy]but-3-en-2-ol

HRID 1375670

Reaction equation

HRID 1375670 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[CH2:14]([OH:19])[CH:15]([OH:18])[CH:16]=[CH2:17]>>[Si:1]([O:19][CH2:14][CH:15]([OH:18])[CH:16]=[CH2:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 103383-Butene-1,2-diolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 109105951-[(Tert-butyldimethylsilyl)oxy]but-3-en-2-ol

Procedure

t-Butyl dimethylsilylchloride (4.28 g, 28.4 mmol) and imidazole (4.83 g, 70.9 mmol) were added to a flask purged with N2 and dichloromethane (50 mL) was added. 3-Butene-1,2-diol (2.50 g, 28.4 mmol) was then added to the flask and the mixture was stirred for 2 hours. The solvent was removed and the titled product (2.71 g, 47.9%) was purified by column chromatography (5% ethyl acetate in hexanes).

Workup

  1. custompurged with N2 and dichloromethane (50 mL)
  2. additionwas added
  3. customThe solvent was removed
  4. customthe titled product (2.71 g, 47.9%) was purified by column chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-96bdca2db0d041aca16efa0e415ac4ad
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Linked notes

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