反応 #171523

反応方程式

3-(13-Bromo-tridecyl)-pyridine

3-picoline

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product

収率 65.0%

3-methyl-1-(13-pyridin-3-yl-tridecyl)-pyridinium bromide

収率 65.0%

反応条件

後処理

1. 1
   温度the mixture was heated at 50 C overnight
2. 2
   その他The excess picoline was removed in vacuum
3. 3
   その他the resulting residue was partitioned between water and ether
4. 4
   洗浄The aqueous layer was washed extensively with ether until no picoline
5. 5
   workup.WAITleft in the aqueous layer
6. 6
   抽出the aqueous layer was extracted with chloroform
7. 7
   その他The chloroform was removed

実験手順

3-(13-Bromo-tridecyl)-pyridine (1 mmol) was added to 3-picoline (5 ml), and the mixture was heated at 50 C overnight. The excess picoline was removed in vacuum, and the resulting residue was partitioned between water and ether. The aqueous layer was washed extensively with ether until no picoline left in the aqueous layer, and then the aqueous layer was extracted with chloroform. The chloroform was removed to afford the product (65%). 1HNMR (300 MHz, CDCl3, ppm), 9.36 (s, 1H), 9.22 (d, J=5.4, 1H), 8.44 (br, 2H), 8.21 (d, J=7.5, 1H), 7.97 (m, 1H), 7.54 (d, 7.2, 1H), 7.24-7.24 m, 1H), 4.96 (t, J=7.2, 2H), 2.58-2.65 M, 5H), 2.00-2.07 (m, 4H), 1.58-1.60 (m, 2H), 1.20-1.36 (m, 16H); 13CNMR, 148.76, 146.10, 145.58, 144.77, 142.38, 139.83, 137.29, 127.80, 123.98, 62.28, 58.71, 33.31, 32.36, 31.32, 29.80, 29.74, 29.64, 29.38, 29.35, 26.45, 19.15, 18.81.

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