반응 #2154

반응 방정식

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

acetylene

→

title compound

수율 95.8%

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

수율 95.8%

용매

ethanol

ethanol

water

반응 조건

후처리

1. 1
   기타remained below 5° C
2. 2
   기타This 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
   추출extracted with ethyl acetate
7. 7
   세척The organic extracts were washed with brine
8. 8
   건조dried (MgSO4)
9. 9
   기타evaporated
10. 10
    기타The residue was purified on silica using 10% ethyl acetate in hexane as eluant

실험 절차

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.

출처