Imidazole → tert-Butyl(dimethyl)[(prop-2-yn-1-yl)oxy]silane

HRID 1616433Notes

Reaction equation

HRID 1616433 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].N1C=CN=C1.[CH3:10][C:11]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])[CH3:12].[Cl-].[NH4+]>ClC(Cl)C>[C:11]([Si:14]([CH3:16])([CH3:15])[O:4][CH2:1][C:2]#[CH:3])([CH3:13])([CH3:12])[CH3:10]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 7859Propargyl alcoholHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 3445622tert-Butyl(dimethyl)[(prop-2-yn-1-yl)oxy]silaneYield 67%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To an ice cooled stirred solution of prop-2-yn-1-ol (10.0 g, 178.3 mmol) and imidazole (18.2 mg, 267.5 mmol) in dichloroethane (500 mL), was added TBDMSCl (40.24 g, 267.5 mmol) and stirring continued at 0° C. for 1.5 h. On completion, saturated aqueous ammonium chloride solution was added to the reaction mixture and extracted with ethyl acetate (3 times). Combined organic layer was dried over sodium sulphate. Removal of the solvent under reduced pressure followed by solvent washings afforded the desired compound (20 g, 67%).

Workup

  1. extractionextracted with ethyl acetate (3 times)
  2. dry with materialCombined organic layer was dried over sodium sulphate
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-6584a8c0e82c470ab52991a244d42512
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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