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

HRID 462382

Reaktionsgleichung

Reaktionsgleichung von HRID 462382
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilaneAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5e65622494834595801ef6ba7857a3f8
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04515727

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