Imidazole → 6-(t-Butyldimethylsilyloxy)-1-hexyne

HRID 1792376Notes

Reaction equation

HRID 1792376 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].N1C=CN=C1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].O>CN(C)C=O>[Si:13]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][C:5]#[CH:6])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 702345-Hexyn-1-ol

Product 1

HCID 110094486-(t-Butyldimethylsilyloxy)-1-hexyneYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hexyne-1-ol (4.81 g, 49.0 mmol) in N,N-dimethylformamide (100 ml) were added imidazole (4.0 g, 59.0 mmol) and t-butyldimethylsilylchloride (8.12 g, 54.0 mmol) at 0° C., which was then stirred at the same temperature for 3 hour After the reaction was completed, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (n-hexane:ethyl acetate=10:1) to give the title compound (10.0 g, yield: 99%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c135dc6d7ce4007b8a2dc6b882435cc
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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