Dimethylformamide → 15-Methoxymethoxy-13-pentadecyne

Participants

Reaction Steps

Propargyl alcohol (3.00 g) was portionwise added to a mixed solution of 2.256 g of sodium hydride and 30 ml of dry dimethylformamide under ice-cooling under a nitrogen atmosphere. The mixture was stirred at room temperature for 30 minutes. The mixture was ice-cooled again and 5.175 g of chloro methyl methyl ether was portionwise added thereto. The mixture was stirred at room temperature overnight. Then, 4.284 g of sodium hydride was added thereto under ice-cooling and the mixture was heated to room temperature, followed by stirring for 30 minutes. The reaction mixture was ice-cooled again and a solution of 26.68 g of lauryl bromide in 20 ml of dry dimethylformamide was portionwise added thereto. The mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted three times with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried over magnesium sulfate anhydride. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography to give 12.374 g of 15-methoxymethoxy-13-pentadecyne.

Provenance & Evidence