Dichloromethane → 1-(12-Cyclohexyldodecyloxy)-3-trityloxy-2-propanol

Participants

Reaction Steps

A mixture of 23.5 g (68.6 mmole) of 1-(12-cyclohexyldodecyloxy)-2,3-propanediol, 28.7 g (103 mmole) of trityl chloride, 13.7 g (137 mmole) of triethylamine and 200 ml of dichloromethane was stirred at room temperature for 2 days. To the reaction mixture was added 10 ml of methanol and the resulting mixture was further stirred for 3 hours. The mixture was washed with water and dried (MgSO4) and the solvent was distilled off to give 52 g (quantitative) of crude 1-(12-cyclohexyldodecyloxy)-3-trityloxy-2-propanol. In 100 ml of tetrahydrofuran (THF) was dissolved 17 g (23 mmole) of this product, and 1.84 g (46 mmole) of 60% sodium hydride was added thereto. The mixture was stirred at room temperature for 1 hour and 4 ml of methyl iodide was added to the mixture. The reaction mixture was stirred at room temperature overnight and then 5 ml of methanol was added thereto. The solvent was distilled off under reduced pressure, and the residue was dissolved in 200 ml of hexane and washed with water and 1N hydrochloric acid, in order. After hexane was distilled off, 30 ml of 1N hydrochloric acid and 60 ml of dioxane were added to the residue, and the mixture was stirred at 80° C. for 10 hours. The mixture was neutralized with sodium bicarbonate and then 60 ml of ethyl acetate was added to the mixture. The resulting mixture was washed with water and dried (MgSO4), and the solvent was distilled off. The residue was subjected to column chromatography on silica gel (200 g) and eluted with dichloromethane-ethyl acetate (5:1) to give 6.6 g (yield: 81%) of the above-mentioned compound as colorless solid.

Provenance & Evidence