Imidazole → Silane, [(8-bromooctyl)oxy](1,1-dimethylethyl)dimethyl-

HRID 654943Notes

Reaction equation

HRID 654943 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>CN(C)C=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1626071-Octanol, 8-bromo-

Product 1

HCID 10969362Silane, [(8-bromooctyl)oxy](1,1-dimethylethyl)dimethyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 8-bromooctan-1-ol (2.15 g, 10.3 mmol), t-butyldimethylsilyl chloride (1.7 g, 11.3 mmol) and imidazole (1.7 g, 25.0 mmol) in dimethylformamide (4 ml) was stirred at room temperature under argon for 48 hours. The reaction was quenched by the addition of water and extracted with hexane. The organic layer was washed with 5% hydrochloric acid, 5% sodium bicarbonate, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a colorless oil. Purification by flash chromatography (silica, 0 to 2% ethyl ether/hexane) gave the desired protected alcohol.

Workup

  1. customThe reaction was quenched by the addition of water
  2. extractionextracted with hexane
  3. washThe organic layer was washed with 5% hydrochloric acid, 5% sodium bicarbonate, water, saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a colorless oil
  8. customPurification by flash chromatography (silica, 0 to 2% ethyl ether/hexane)
  9. customgave the

Sources & evidence

ORD record
ord-a663ba6f2ab14cef8f8991d91eea4f7c
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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