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

HRID 979386Notes

Reaction equation

HRID 979386 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[C:5]([Si:9](Cl)([CH3:11])[CH3:10])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:10][Si:9]([CH3:11])([C:5]([CH3:8])([CH3:7])[CH3:6])[O:4][CH2:1][C:2]#[CH:3]

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of propargyl alcohol (8.7 ml), t-butyldimethyl silyl chloride (25. g) and 4-dimethylaminopyridine (0.73 g) in methylene chloride (45 ml) was cooled to 0°. Triethylamine (25.1 ml) was added dropwise over 5 mins with stirring. After 18 h the mixture was diluted with methylene chloride (50 ml) and extracted with water (2×75 ml). The aqueous solutions were combined and then extracted with methylene chloride (25 ml). The organic phases were combined and washed with water and saturated aqueous ammonium chloride, dried and evaporated to give an oil (24.9 g). Distillation under reduced pressure afforded the title compound as an oil (20.8 g); bp 60°-62° (24 mm Hg).

Workup

  1. extractionextracted with water (2×75 ml)
  2. extractionextracted with methylene chloride (25 ml)
  3. washwashed with water and saturated aqueous ammonium chloride
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-595bdae197bb405484bac172bd2a66d9
Source dataset
uspto-grants-1987_05
Patent number
US04666899

Reaction notes

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