Hydrochloric Acid → Methyl 5-methoxy-3-methyl-1-benzofuran-2-carboxylate

To a mixture of 1-(2-hydroxy-5-methoxyphenyl)ethanone (5.00 g), methyl bromoacetate (3.13 mL) and N,N-dimethylformamide (50 mL) was added potassium carbonate (12.5 g), and the mixture was stirred overnight at room temperature. Water was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a brown oil. To a solution (50 mL) of the obtained oil in methanol was added sodium methoxide (1.63 g), and the mixture was stirred with heating under reflux for 3 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (1.25 g, 19%) as a white solid.

1. customto quench
2. customthe reaction
3. extractionthe reaction mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customto give a brown oil
8. stirringthe mixture was stirred
9. temperaturewith heating
10. temperatureunder reflux for 3 hr
11. customto quench
12. customthe reaction
13. extractionthe mixture was extracted with ethyl acetate
14. washThe extract was washed with saturated brine
15. dry with materialdried over magnesium sulfate
16. concentrationconcentrated under reduced pressure
17. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)

ORDレコード

ord-cbedb24a2a044ee6855558216ddb7020

出典データセット

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08436043B2