Water → HCID 19880359, compound

Participants

Reaction Steps

0.8 g of acetic anhydride was added to a mixture of 0.9 g of 5-{4-[4-(2,5-dihydroxy-3,4,6-trimethylphenyl)-2-hydroxy-2-methylbutoxy]benzyl}-2,4-dioxothiazolidine (prepared as described in Example 3) and 7 ml of pyridine, and the resulting mixture was allowed to stand at room temperature for 3 days. At the end of this time, the reaction mixture was poured into 50 ml of water and then extracted with ethyl acetate. The extracts were washed, in turn, with 0.1N aqueous hydrochloric acid and with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure. The resulting residue was then subjected to column chromatography through silica gel, using a 7:3 by volume mixture of benzene and ethyl acetate as the eluent, to afford 0.3 g of the title compound as a white powder softening at 94°-97° C.

Provenance & Evidence