Imidazole → 1-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-

HRID 2080733Notes

Reaction equation

HRID 2080733 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].N1C=CN=C1.[C:12]([Si:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)Cl)([CH3:15])([CH3:14])[CH3:13]>CN(C=O)C>[Si:16]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])([C:12]([CH3:15])([CH3:14])[CH3:13])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 80641,4-ButanediolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 100651081-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-Yield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (120 ml), 1,4-butanediol (4.0 g) was dissolved. The solution was added with imidazole (3.02 g) and t-butyldiphenylchloro silane (12.2 g), and the whole was stirred at room temperature for 15 hours. The reaction solution was concentrated under reduced pressure and then added with a saturated aqueous ammonium chloride solution, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (hexane/ethyl acetate) thereby obtaining the subject compound (6.56 g) as a colorless oily substance.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionadded with a saturated aqueous ammonium chloride solution
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f7e89168cbd14042b49fc630084bac8a
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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