Lithium → HCID 22602338, compound

Participants

Reaction Conditions

Reaction Steps

To anhydrous 1,3-diaminopropane (180 ml), which had been distilled, metallic lithium (2.8 g, 0.4 mol) was added under argon stream, and the mixture was stirred for 2 hours at 70° C. After the mixture was allowed to cool, potassium t-butoxide (27 g, 0.24 mol) was added, followed by stirring for 15 minutes. The 6-methyl-2-pentadecyne (6″) (12.1 g, 54.5 mmols) was added dropwise, and the mixture was stirred overnight at room temperature. This reaction was carefully quenched with a saturated aqueous solution of ammonium chloride, and then the mixture was extracted with ether. The resulting organic layer was washed (diluted hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride), dried (magnesium sulfate), and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 6-methyl-1-pentadecyne (7″) (9.90 g, 82%). IR and 1H-NMR analysis of the product showed the following results: IR (film) 3300 (m,C≡CH), 2130 cm−1 (w,C≡C). 1H-NMR (90 MHz, CDCl3) 0.84 (3H,d,J=7,6-Me), 0.88 (3H,t,J=7,15-H), 1.0-1.6 (21H,m,4˜14-H), 1.93 (1H,t,J=2.5,1-H), 2.0-2.3 (2H,m,3-H).

Provenance & Evidence