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

HRID 2288870Notes

Reaction equation

HRID 2288870 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].N1C=CC=CC=1>C(Cl)Cl>[Si:6]([O:5][CH2:1][CH2:2][C:3]#[CH:4])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 135663-Butyn-1-OLHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-butyne-1-ol (5.0 g; 71.3 mmol) in ca. 75 ml of methylene chloride was added tert-butydimethylsilyl chloride (10.8 g; 71.6 mmol) and 7 ml of pyridine. The mixture was allowed to stir overnight at room temperature, diluted with methylene chloride, washed with water, 1M HCl, brine and dried (Na2SO4). Concentration in vacuo afforded the title compound as a colorless liquid.

Workup

  1. washwashed with water, 1M HCl, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-2201f5c9e3074dd7923f6de2b807a9b9
Source dataset
uspto-grants-2000_07
Patent number
US06090839

Reaction notes

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