반응 #171501

반응 방정식

(8-Bromo-octyl)-benzene

4-picoline

→

product

수율 78.0%

4-methyl-1-(8-phenyl-octyl)-pyridinium bromide

수율 78.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도the solution was refluxed for 24 hours
2. 2
   기타The acetonitrile was removed in vacuum
3. 3
   기타the resulting residue was partitioned between ether and water
4. 4
   세척The aqueous layer was washed extensively with ether until no picoline
5. 5
   workup.WAITwas left in the aqueous layer
6. 6
   추출The resulting aqueous solution of the product was extracted with chloroform
7. 7
   기타The chloroform was removed

실험 절차

(8-Bromo-octyl)-benzene (1 mmol) was added to a solution of 4-picoline (3 mmol) in acetonitrile, and the solution was refluxed for 24 hours. The acetonitrile was removed in vacuum and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no picoline was left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (78%). 1HNMR (300 MHz, CDCl3, ppm) 9.26 (d, 2H), 7.84 (d, 2H), 7.14-7.28 (dd, 4H), 4.90 (t, 2H), 2.62 (s, 3H), 2.56 (t, 2H), 1.92-2.02 (m, 2H), 1.50-1.60 (m, 2H), 1.20-1.40 (br, 8H). 13CNMR, 158.92, 144.28, 142.86, 128.95, 128.56, 128.40, 125.76, 61.61, 36.19, 32.15, 31.71, 29.53, 29.42, 29.31, 26.37, 22.63.

출처