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

HRID 2249272Notes

Reaction equation

HRID 2249272 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[Si:7](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C=CN=C1.O>CN(C)C=O>[O:5]([CH2:4][CH2:3][CH2:2][CH2:1][OH:6])[Si:7]([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 80641,4-ButanediolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 100651081-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-Yield 64.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.00 g (10.2 mmol) of 1,4-butanediol in 20 ml of dry dimethylformamide were added 2.80 g (10.2 mmol) of tert-butyldiphenylsilyl chloride and 3.47 g (51.0 mmol) of imidazole in an atmosphere of argon. The mixture was allowed to react at 0° C. for 24 hours. To the solution was added water followed by extraction with dichloromethane. The organic layer was washed with water and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-methanol (100:1) yielded 2.17 g (6.62 mmol) of 4-(tert-butyldiphenylsiloxy)-1-butanol.

Workup

  1. customto react at 0° C. for 24 hours
  2. extractionfollowed by extraction with dichloromethane
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas subjected to silica gel column chromatography for separation and purification
  7. washElution with dichloromethane-methanol (100:1)

Sources & evidence

ORD record
ord-ef9ad2f5497f4489940e4f5344d1aa09
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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