반응 #8872

반응 방정식

methyl trans-3-fluorocinnamate

2-((trimethylsilyl)methyl)-2-propen-1-yl acetate

→

title compound

수율 83.9%

Methyl (±)-trans-4-methylene-2-(3-fluorophenyl)cyclopentanoate

수율 83.9%

용매

THF

hexane

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to reflux for 6 h
3. 3
   여과filtered
4. 4
   기타to remove the yellow precipitate
5. 5
   기타The volatiles were then removed in vacuo
6. 6
   기타the residue was purified by FC (3 to 5% ethyl acetate in hexanes)

실험 절차

A mixture of methyl trans-3-fluorocinnamate (41.25 g, 229 mmol), tetrakis(triphenylphosphine) palladium(0) (18.5 g, 16 mmol), 1,2-bis(diphenylphosphino)ethane (5.5 g, 13.7 mmol), and 2-((trimethylsilyl)methyl)-2-propen-1-yl acetate (42.66 g, 229 mmol) in THF (300 mL) under nitrogen was heated to reflux for 6 h and then stirred at room temperature for 16 h. The reaction was diluted with hexane and filtered to remove the yellow precipitate. The volatiles were then removed in vacuo and the residue was purified by FC (3 to 5% ethyl acetate in hexanes) to afford the title compound (45 g).

출처