反应 #2154

反应方程式

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

acetylene

→

title compound

收率 95.8%

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

收率 95.8%

溶剂

ethanol

ethanol

water

反应条件

后处理

1. 1
   其他remained below 5° C
2. 2
   其他This 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
   萃取extracted with ethyl acetate
7. 7
   洗涤The organic extracts were washed with brine
8. 8
   干燥dried (MgSO4)
9. 9
   其他evaporated
10. 10
    其他The residue was purified on silica using 10% ethyl acetate in hexane as eluant

实验过程

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.

来源