Reaktion #552644

Reaktionsgleichung

Methyl 5-chloromethyl-2-furoate

4-hydroxyphenyl propan-2-one

potassium carbonate

potassium iodide

→

methyl 5-[4-acetonyl- phenoxymethyl]furan-2-carboxylate

Lösungsmittel

acetone

methanol

hydrochloric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturunder reflux for 4 hr
3. 3
   Temperatur, cooled
4. 4
   Filtrationfiltered
5. 5
   SonstigeThe filtrate was evaporated to an oil which
6. 6
   Sonstigewas purified by column chromatography on silica gel
7. 7
   WaschenElution with chloroform
8. 8
   Sonstigegave a crystalline solid which
9. 9
   workup.STIRRINGwas stirred at ambient temperature for 4 hr
10. 10
    SonstigeThe methanol was evaporated
11. 11
    Extraktionthe aqueous residue was extracted into dichloromethane
12. 12
    ExtraktionThe organic extract
13. 13
    Trocknenwas dried (MgSO4)
14. 14
    Sonstigeevaporated

Vorschrift

Methyl 5-chloromethyl-2-furoate (4.5 g) was added to a mixture of 4-hydroxyphenyl propan-2-one, ethylene ketal (5 g) and potassium carbonate (3.56 g) in acetone (150 ml) containing a catalytic amount of potassium iodide. The reaction mixture was stirred and heated under reflux for 4 hr., cooled and filtered. The filtrate was evaporated to an oil which was purified by column chromatography on silica gel. Elution with chloroform gave a crystalline solid which was stirred at ambient temperature for 4 hr. in a mixture of methanol (50 ml) and 2N hydrochloric acid (50 ml). The methanol was evaporated and the aqueous residue was extracted into dichloromethane. The organic extract was dried (MgSO4) and evaporated to give methyl 5-[4-acetonyl- phenoxymethyl]furan-2-carboxylate as an oil.

Quelle