Methanol → HCID 19835441, compound

Participants

Reaction Steps

Then 1.8 g (6.12 millimole) of this epoxy derivative was converted into crude 1-O-(hexadecyn-14-yl)-3-O-[2-(2-trityloxyethoxyethoxy)ethyl]glycerol by following the procedure described in Working Example 62. The crude product was dissolved in 20 ml of THF, to which 367 mg (9.18 millimole) of 60% sodium hydride was added, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added dropwise 1.74 g (12.2 millimole) of methyl iodide in 4 ml of THF over a period of 20 minutes. The reaction mixture was stirred at room temperature overnight, to which was added 1 ml of methanol, and the mixture was concentrated under reduced pressure. The residue was extracted with hexane, and the hexane layer was washed with water, and then hexane was distilled off. To the residue were added 45 ml of dioxane, 30 ml of methanol and 12 ml of 2N hydrochloric acid, and the mixture was stirred at 70° C. for 1 hour. The reaction mixture was cooled, neutralized with saturated aqueous solution of sodium hydrogencarbonate, and concentrated under reduced pressure, and then the residue was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was distilled off. The residue was subjected to silica gel (50 g) column chromatography, and eluted with chloroform-methanol (9:1), to give the above-captioned compound as colorless oil.

Provenance & Evidence