Epichlorohydrin → 1-hydroxy-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one

Participants

Reaction Conditions

Reaction Steps

1,3-dihydroxy-9H-xanthen-9-one (1 g, 4.39 mmol) prepared in Step 1 of Example 2 and K2CO3 (1.52 g, 10.98 mmol) were added to a dry round-bottom flask, and anhydrous acetone (25 ml) was added thereto. Epichlorohydrin (1.73 mL, 21.95 mmol) was added dropwise to the reaction mixture, and the reaction liquid was stirred under reflux at a temperature of 55 to 60° C. for 6 hours. After the reaction was completed, the solvent was removed under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1 (v/v)) to give the title compound (0.28 g, 22%) as a light brown solid.

Provenance & Evidence