Methanol → HCID 9957850, compound

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Reaction Steps

To 250 mL methanol was added 4-benzo[1,3]dioxol-5-ylmethyl-5-hydroxy-3-(4-methoxy-phenyl)-5-(3,4,5-trimethoxy-phenyl)-5H-furan-2-one 4.0 g (7.89 mmol), giving solution. To the solution was added 250 mL water containing 15.8 mL 1.001N NaOH. The solution was irradiated with a Hanovia ultraviolet light contained in a quartz reactor (Ace Glass, Catalog 1200, #7840-180) for 16 hours at ambient temperature. The solution was evaporated in vacuo to remove the methanol. The residual aqueous solution was extracted repeatedly with ethyl ether, while the pH of the aqueous phase was adjusted incrementally between 7.5 and 8 by addition of 3N HCl. The aqueous phase was then acidified to pH 1 with HCl and extracted with ethyl ether. The ether extract was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Evaporation of the ether solution under reduced pressure gave a foam, 1.44 g. The residue was purified by chromatography on 50 g silica gel eluted with 1% methanol in chloroform. The appropriate fractions were evaporated to a solid, 0.77 g. The product was identified by 1H NMR, MS [M-H]+ =505.4 Da. and microanalysis.

Provenance & Evidence