Potassium Iodide → 1-Dodec-7-ynyl-2,4-dimethyl-pyridinium iodide

Participants

Reaction Steps

12-Chloro-dodec-5-yne (1 mmol) was mixed with potassium iodide (3 mmol) and 2,4-lutidine (3 mmol) in butanone. The mixture was refluxed for 3 days and cooled to room temperature, filtrated. The butanone was removed in a vacuum, and the resulting residue was partitioned between water and ethyl ether. The aqueous layer was washed extensively with ether until no 2,4-lutidine 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 (84%). 1HNMR (300 MHz, CDCl3, ppm), 9.40 (d, 1H), 7.75 (d, 1H), 7.66 (s, 1H), 4.78 (t, 3H), 2.88 (s, 3H), 2.60 (s, 3H), 2.05-2.15 (br, 4H), 1.80-2.00 (br, 2H), 1.30-1.50 (br, 10H), 0.86 (t, 3H); 13CNMR, 156.73, 153.05, 145.84, 136.61, 127.27, 80.86, 79.85, 58.12, 31.54, 30.94, 39.09, 26.17, 22.39, 22.30, 21.03, 18.96, 18.79, 14.02.

Provenance & Evidence