تفاعل #170272

معادلة التفاعل

1,3-dihydroxy-5-methoxy-9H-xanthen-9-one

K2CO3

epichlorohydrin

→

title compound

المردود 32.1%

1-hydroxy-5-methoxy-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one

المردود 32.1%

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas charged to a dry round-bottom flask
2. 2
   ترشيحSolid of the reaction mixture was filtered
3. 3
   أخرىthe solvent was removed under reduced pressure
4. 4
   أخرىThe resulting residue was separated
5. 5
   أخرىpurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1 (v/v))

الإجراء التجريبي

A mixture of 1,3-dihydroxy-5-methoxy-9H-xanthen-9-one (1.13 g, 4.39 mmol) prepared in Step 1 of Example 1 and K2CO3 (1.52 g, 10.98 mmol) in anhydrous acetone (25 mL) was charged to a dry round-bottom flask, and epichlorohydrin (1.73 mL, 21.95 mmol) was added thereto, followed by stirring under reflux at a temperature of 55 to 60° C. for 6 hours. Solid of the reaction mixture was filtered, and 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 (443.2 mg, 32%) as a light yellow solid.

المصدر