Hydrochloric Acid → HCID 58786227, compound

Participants

Reaction Steps

28% methanol solution of sodium methoxide (0.5 ml) was added to a solution of methyl 2-[3-(chloromethyl)-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yl]benzyl]azulene-1-carboxylate (0.06 g) in methanol (3.0 ml) at room temperature. The mixture was stirred for one hour. 10% aqueous solution of sodium hydroxide (3.0 ml) was further added to the reaction mixture and the mixture was refluxed with heating for one hour. After cooling to room temperature, the reaction mixture was neutralized by adding 10% aqueous solution of hydrochloric acid, extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain (1S)-1,5-anhydro-1-[3-(azulen-2-ylmethyl)-5-(methoxymethyl)phenyl]-D-glucitol (0.02 g).

Provenance & Evidence