反応 #515394

反応方程式

methyl 4-bromobenzoate

triphenylphosphine

trimethylsilylacetylene

→

Methyl 4-trimethylsilylethynylbenzoate

溶媒

triethylamine

反応条件

後処理

1. 1
   workup.ADDITIONare introduced into a three-necked flask under a stream of nitrogen
2. 2
   温度The reaction medium is cooled
3. 3
   ろ過the salt is filtered off
4. 4
   その他the filtrate is evaporated
5. 5
   その他The ether phase is separated out after settling
6. 6
   洗浄washed with water
7. 7
   乾燥dried over magnesium sulphate
8. 8
   その他evaporated
9. 9
   その他The residue obtained
10. 10
    その他is purified by chromatography on a column of silica
11. 11
    洗浄eluted with dichloromethane
12. 12
    その他After evaporation of the solvents, 23 g (100%) of the expected derivative
13. 13
    その他are collected in the form of a colourless oil

実験手順

21.5 g (0.1 mol) of methyl 4-bromobenzoate, 300 ml of triethylamine and a mixture of 200 mg of palladium acetate and 400 mg of triphenylphosphine are introduced into a three-necked flask under a stream of nitrogen. 20 g (0.20 mol) of trimethylsilylacetylene are then added, the mixture is heated gradually to 90° C. over 1 hour and left at this temperature for 5 hours. The reaction medium is cooled, the salt is filtered off and the filtrate is evaporated. The residue is taken up in 200 ml of hydrochloric acid (5%) and 400 ml of ethyl ether. The ether phase is separated out after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with dichloromethane. After evaporation of the solvents, 23 g (100%) of the expected derivative are collected in the form of a colourless oil.

出典