Pyridine → trans-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-(4-fluoro-3-isopropenylbenzyl)amine

Participants

Reaction Conditions

Reaction Steps

Compound 29 (0.55 g; 1.73 mmol) and phosphorus oxychloride (1.33 g; 8.65 mmol) were dissolved in pyridine (25 ml). The solution was stirred for 3 hours at 110° C., and left to cool to room temperature. The mixture was poured into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with diethyl ether (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby yield 0.17 g of the target compound (yield: 32.8%).

Provenance & Evidence