反应详情

3-(13-Bromo-tridecyl)-pyridine (1 mmol) was added to 3,4-lutidine (5 ml), and the mixture was heated at 50 C overnight. The excess picoline was removed in a vacuum, and the resulting residue was partitioned between water and ether. The aqueous layer was washed extensively with ether until no 3,4-lutidine was left in the aqueous layer, and then the aqueous layer was extracted with chloroform. The chloroform was removed to afford the product (60%). 1HNMR (300 MHz, CDCl3, ppm), 9.23 (s, 1H), 9.04 (d, J=6.3, 1H), 8.40 (br, 2H), 7.79 (d, J=6.0, 1H), 7.48 (d, 8.1, 1H), 7.18-7.20 (m, 1H), 4.83 (t, J=7.5, 2H), 2.58 (t, J=7.5, 2H), 2.52 (s, 3H), 2.49 (s, 3H), 2.21 (br, 1H), 1.82-2.02 (m, 2H), 1.54-1.62 (m, 2H), 1.15-1.35 (br, 12H). 13CNMR, 157.61, 149.68, 146.92, 143.35, 141.91, 138.45, 138.33, 136.32, 128.65, 123.57, 61.37, 33.31, 32.19, 31.41, 29.85, 29.80, 29.68, 29.41, 26.45, 20.69, 17.40.

1. temperaturethe mixture was heated at 50 C overnight
2. customThe excess picoline was removed in a vacuum
3. customthe resulting residue was partitioned between water and ether
4. washThe aqueous layer was washed extensively with ether until no 3,4-lutidine
5. waitwas left in the aqueous layer
6. extractionthe aqueous layer was extracted with chloroform
7. customThe chloroform was removed