Imidazole → (But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

HRID 462382

Reaction equation

HRID 462382 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].N1C=CN=C1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]>CN(C)C=O>[Si:11]([O:5][CH2:1][CH2:2][C:3]#[CH:4])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 135663-Butyn-1-OLHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilaneYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 21 g of 3-butyn-1-ol and 27 g of imidazole in 100 ml of dimethyl formamide was treated with 45 g of t-butyldimethylsilyl chloride in several portions over a one hour period. After stirring under nitrogen for 18 hours the reaction mixture was diluted with 500 ml of ice water. The resulting aqueous solution was extracted with 300 ml of ether and the ethereal solution washed with water and then brine. The ethereal solution was dried over potassium carbonate. Evaporation of the ether and distillation of the residue gave 47.6 g of 3-butyn-1-ol t-butyldimethylsilyl ether, bp 80°-83° C./25 mm.

Workup

  1. extractionThe resulting aqueous solution was extracted with 300 ml of ether
  2. washthe ethereal solution washed with water
  3. dry with materialThe ethereal solution was dried over potassium carbonate
  4. customEvaporation of the ether and distillation of the residue

Sources & evidence

ORD record
ord-5e65622494834595801ef6ba7857a3f8
Source dataset
uspto-grants-1985_05
Patent number
US04515727

Linked notes

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