Propyne → HCID 22602329, compound

Participants

Reaction Conditions

Reaction Steps

Tetramethylethylenediamine (TMEDA) (15 ml) was added to a THF (80 ml) solution of propyne (about 4 g, 0.1 mol) under argon. To the mixture, n-BuLi (1.55 M, 64.5 ml, 100 mmols) was added dropwise at −78° C. With the temperature being raised gradually to 0° C., the mixture was stirred for 1.5 hours, and then cooled again to −78° C. Thereto, an HMPA-THF (20 ml+20 ml) solution of the 1-bromo-3-methyldodecane (5″) (13.2 g, 50 mmols) was added dropwise, and with the temperature of the mixture being raised gradually to room temperature, stirring was continued overnight. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and extracted with hexane. The resulting organic layer was washed (water, 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-2-pentadecyne (6″) (12.1 g, 97%). 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 (19H,m,5˜14-H), 1.77 (3H,t,J=2.5,1-H), 2.12 (2H,m,4-H).

Provenance & Evidence