反应详情

To a nitrogen flushed 5 L three neck round bottom flask fitted with a mechanical stirrer, condenser, and a nitrogen inlet was charged 326 g (1.68 mol) of methyl 4-hydoxy-3-n-propylbenzoate, 507.6 g (1.73 mol) of ethyl α-bromo-3,4-methylenedioxyphenylacetate from above, 235 g (1.70 mol) of anhydrous potassium carbonate, and 1.7 L of acetone. The mixture was refluxed with vigorous stirring for 9 hr. The suspension was allowed to cool to ambient temperature and stirred overnight. The mixture diluted with 2 L of ether, cooled to 0° C. and filtered through Super-Cel®. The cake washed with ether and the combined filtrate concentrated. The residue was redissolved in ether and the organic layer washed with once with 1N HCl, saturated sodiuim bicarbonate solution, 10% sodium bisulfite solution, brine, dried with magnesium sulfate, treated with charcoal and filtered through a plug of silica. The pale yellow solution was concentrated to 7.3 g (theoretical 678 g) of a thick yellow oil which was used without purification in the next step. NMR was consistent with the title compound.

1. customTo a nitrogen flushed 5 L three neck round bottom flask
2. customfitted with a mechanical stirrer, condenser, and a nitrogen inlet
3. temperatureThe mixture was refluxed
4. stirringstirred overnight
5. temperaturecooled to 0° C.
6. filtrationfiltered through Super-Cel®
7. washThe cake washed with ether
8. concentrationthe combined filtrate concentrated
9. dissolutionThe residue was redissolved in ether
10. washthe organic layer washed with once with 1N HCl, saturated sodiuim bicarbonate solution, 10% sodium bisulfite solution, brine
11. dry with materialdried with magnesium sulfate
12. additiontreated with charcoal
13. filtrationfiltered through a plug of silica
14. concentrationThe pale yellow solution was concentrated to 7.3 g (theoretical 678 g) of a thick yellow oil which
15. customwas used without purification in the next step