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

HRID 1174016Notes

Reaction equation

HRID 1174016 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

Commercially available 1,4-butanediol (400 g) was dissolved in DMF (120 ml), added with imidazole (3.02 g) and t-butyldiphenylchlorosilane (12.2 g), and 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 separation/extraction with chloroform. The organic layer was washed with 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 transparent and 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 separation/extraction with chloroform
  4. washThe organic layer was washed with 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-f3a309bac19b415e94ed9df0ee666596
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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