Reaktion #87299

Reaktionsgleichung

1-pentyne

ethyl(3-bromophenyl)acetate

tetrabutylammonium fluoride hydrate

→

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

Ausbeute 80.5%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionwas extracted with diethyl ether
2. 2
   ExtraktionThe organic extract
3. 3
   Trocknenwas dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated in vacuo
6. 6
   Sonstigeto give the crude product
7. 7
   SonstigePurification on a Biotage™ 25 M column (silica)
8. 8
   Wascheneluting with ethyl acetate/hexane 0:1 to 2:98

Vorschrift

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%).

Quelle