Reaktion #2154

Reaktionsgleichung

2-Phenyl-4-trimethylsilyl-but-3-yn-1-ol

acetylene

→

title compound

Ausbeute 95.8%

2-Phenyl-but-3-yn-1-ol

Ausbeute 95.8%

Lösungsmittel

ethanol

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeremained below 5° C
2. 2
   SonstigeThis precipitated the acetylene as the silver complex
3. 3
   workup.ADDITIONA solution of potassium cyanide (17 g) in water (30 ml) was added dropwise to the stirred acetylene mixture
4. 4
   workup.DISSOLUTIONThe mixture mainly dissolved
5. 5
   workup.ADDITIONwas diluted with water
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   WaschenThe organic extracts were washed with brine
8. 8
   Trocknendried (MgSO4)
9. 9
   Sonstigeevaporated
10. 10
    SonstigeThe residue was purified on silica using 10% ethyl acetate in hexane as eluant

Vorschrift

2-Phenyl-4-trimethylsilyl-but-3-yn-1-ol (Chem. Ber. (1988), 121, 1315-1320) (7.8 g) was dissolved in ethanol and the solution was cooled to -5° C. A solution of silver nitrate (8.9 g) in ethanol (60 ml) and water (21 ml) was added dropwise to the acetylene solution such that the temperature remained below 5° C. This precipitated the acetylene as the silver complex. A solution of potassium cyanide (17 g) in water (30 ml) was added dropwise to the stirred acetylene mixture and the resulting mixture was stirred at room temperature for 30 minutes. The mixture mainly dissolved and was diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4) and evaporated. The residue was purified on silica using 10% ethyl acetate in hexane as eluant to afford the title compound (5 g) as a colourless oil.

Quelle