تفاعل #2154

معادلة التفاعل

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

acetylene

→

title compound

المردود 95.8%

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

المردود 95.8%

المذيبات

ethanol

ethanol

water

ظروف التفاعل

المعالجة

1. 1
   أخرىremained below 5° C
2. 2
   أخرىThis 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
   استخلاصextracted with ethyl acetate
7. 7
   غسيلThe organic extracts were washed with brine
8. 8
   تجفيفdried (MgSO4)
9. 9
   أخرىevaporated
10. 10
    أخرىThe residue was purified on silica using 10% ethyl acetate in hexane as eluant

الإجراء التجريبي

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.

المصدر