반응 #87299

반응 방정식

1-pentyne

ethyl(3-bromophenyl)acetate

tetrabutylammonium fluoride hydrate

→

ethyl (3-(pentyne-1-yl)phenyl)acetate

수율 80.5%

용매

water

반응 조건

후처리

1. 1
   추출was extracted with diethyl ether
2. 2
   추출The organic extract
3. 3
   건조was dried over sodium sulfate
4. 4
   여과filtered
5. 5
   기타evaporated in vacuo
6. 6
   기타to give the crude product
7. 7
   기타Purification on a Biotage™ 25 M column (silica)
8. 8
   세척eluting with ethyl acetate/hexane 0:1 to 2:98

실험 절차

A mixture of ethyl(3-bromophenyl)acetate (0.3 g, 1.24 mmol) and tetrabutylammonium fluoride hydrate (0.97 g, 3.72 mmol), was treated with PdCl2(PPh3)2 (26 mg, 0.037 mmol; 3 mole %) and 1-pentyne (367 μL, 3.72 mmol) in a sealed tube. The tube was heated at 80° C. for 2 h. The mixture was treated with water, and was extracted with diethyl ether. The organic extract was dried over sodium sulfate, filtered and evaporated in vacuo to give the crude product. Purification on a Biotage™ 25 M column (silica), eluting with ethyl acetate/hexane 0:1 to 2:98, gave ethyl (3-(pentyne-1-yl)phenyl)acetate as a pale yellow oil (0.23 g, 79%).

출처