12-chlorododec-5-yne

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 12-Chloro-dodec-5-yne (1 mmol) was mixed with Sodium iodide (3 mmol) and 3,4-lutidine (3 mmol) in butanone. The mixture was refluxed for 3 days and cooled to room temperature, filtrated. The butanone was removed in vacuum, and the resulting residue was partitioned between water and ethyl ether. The aqueous layer was washed extensively with ether until no 3,4-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 (72%). 1HNMR, (300 MHz, CDCl3, ppm, ppm), 9.22 (s, 1H), 9.04 (d, 1H), 7.80 (d, 1H), 4.84 (t, 3H), 2.52 (s, 3H), 2.50 (s, 3H), 1.92-2.14 (m, 6H), 1.28-1.45 (m, 10H), 0.84 (t, 3H). 13CNMR, 157.84, 143.39, 141.81, 138.53, 128.72, 80.80, 79.90, 61.23, 32.03, 31.54, 29.08, 28.48, 25.91, 22.30, 20.78, 18.96, 18.79, 17.44, 14.02. The mixture was refluxed for 3 days filtrated The butanone was removed in vacuum the resulting residue was partitioned between water and ethyl ether The aqueous layer was washed extensively with ether until no 3,4-lutidine was left in the aqueous layer The resulting aqueous solution of the product was extracted with chloroform The chloroform was removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 12-Chloro-dodec-5-yne (1 mmol) was mixed with potassium iodide (3 mmol) and 3,5-lutidine (3 mmol) in butanone. The mixture was refluxed for 3 days and cooled to room temperature, filtrated. The butanone was removed in vacuum, and the resulting residue was partitioned between water and ethyl ether. The aqueous layer was washed extensively with ether until no 3,5-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 (78%). 1HNMR (300 MHz, CDCl3, ppm), 9.06 (s, 2H), 8.00 (s, 1H), 4.86 (t, 3H), 2.48 (s, 3H), 1.98-2.16 (m, 6H), 1.32-1.48 (br, 10H), 0.88 (t, 3H); 13CNMR, 146.12, 141.38, 138.64, 80.43, 79.53, 61.46, 31.70, 31.17, 28.68, 28.07, 25.55, 21.92, 18.57, 18.42, 13.63. The mixture was refluxed for 3 days filtrated The butanone was removed in vacuum the resulting residue was partitioned between water and ethyl ether The aqueous layer was washed extensively with ether until no 3,5-lutidine was left in the aqueous layer The resulting aqueous solution of the product was extracted with chloroform The chloroform was removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The mixture was refluxed for 3 days filtrated The butanone was removed in a vacuum 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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 12-Chloro-dodec-5-yne (1 mmol) was mixed with potassium iodide (3 mmol) and 4-picoline (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 4-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 (87%). 1HNMR (300 MHz, CDCl3, ppm), 9.28 (d, 2H), 7.92 (d, 2H), 4.92 (t, 2H), 2.68 (s, 3H), 1.96-2.18 (m, 6H), 1.32-1.50 (br, 10H), 0.88 (t, 3H). The mixture was refluxed for 3 days filtrated The butanone was removed in a vacuum the resulting residue was partitioned between water and ethyl ether The aqueous layer was washed extensively with ether until no 4-picoline was left in the aqueous layer The resulting aqueous solution of the product was extracted with chloroform The chloroform was removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 12-Chloro-dodec-5-yne (1 mmol) was mixed with potassium iodide (3 mmol) and 3-picoline (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 3-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 (82%). 1HNMR (300 MHz, CDCl3, ppm) 9.36 (s, 1H), 9.18 (d, 1H), 8.24 (d, 1H), 8.00 (dd, 1H), 4.92 (t, 2H), 2.62 (s, 3H), 1.95-2.18 (m, 6H), 1.15-1.25 (br, 10H), 0.90 (t, 3H); 13CNMR, 145.51, 144.12, 144.78, 139.46, 127.56, 80.44, 79.42, 61.75, 31.72, 31.16, 28.65, 28.04, 25.52, 21.92, 18.75, 18.55, 18.40, 13.63. The mixture was refluxed for 3 days filtrated The butanone was removed in a vacuum the resulting residue was partitioned between water and ethyl ether The aqueous layer was washed extensively with ether until no 3-picoline was left in the aqueous layer The resulting aqueous solution of the product was extracted with chloroform The chloroform was removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 12-Chloro-dodec-5-yne (1 mmol) was mixed with potassium iodide (3 mmol) and 2-picoline (3 mmol) in butanone. room temperature. 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-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 (85%). 1HNMR (300 MHz, CDCl3, ppm) 9.62 (d, 1H), 8.39 (dd, 1H), 7.99 (m, 1H), 7.91 (d, 1H), 4.88 (t, 2H), 2.97 (s, 3H), 2.12-2.20 m, 4H), 1.90-2.00 (m, 2H), 1.32-1.58 (m, 8H), 0.88 (t, 3H). room temperature The butanone was removed in a vacuum the resulting residue was partitioned between water and ethyl ether The aqueous layer was washed extensively with ether until no 2-picoline was left in the aqueous layer The resulting aqueous solution of the product was extracted with chloroform The chloroform was removed