تفاعل #87299

معادلة التفاعل

1-pentyne

ethyl(3-bromophenyl)acetate

tetrabutylammonium fluoride hydrate

→

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

المردود 80.5%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصwas extracted with diethyl ether
2. 2
   استخلاصThe organic extract
3. 3
   تجفيفwas dried over sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   أخرىevaporated in vacuo
6. 6
   أخرىto give the crude product
7. 7
   أخرىPurification on a Biotage™ 25 M column (silica)
8. 8
   غسيلeluting with ethyl acetate/hexane 0:1 to 2:98

الإجراء التجريبي

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%).

المصدر