Hydrochloric Acid → 2-Ethyl-5-(1-ethylpropyl)thiophene-3-carbaldehyde

To a solution (40 mL) of ethyl 2-ethyl-5-(1-ethylpropyl)thiophene-3-carboxylate (1.98 g) synthesized above in tetrahydrofuran was added 1.5M diisobutylaluminum hydride-toluene solution (15.5 mL) at 0° C., and the mixture was stirred for 1 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and brine, dried over magnesium sulfate and concentrated under reduced pressure to give a colorless oil. To a solution of the obtained oil in tetrahydrofuran (40 mL) was added activated manganese dioxide (10.0 g), and the mixture was stirred at room temperature overnight. Manganese dioxide was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19, volume ratio) to give the title compound (1.40 g, 86%) as a yellow oil.

1. customto quench
2. customthe reaction
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with 1N hydrochloric acid and brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customto give a colorless oil
8. stirringthe mixture was stirred at room temperature overnight
9. filtrationManganese dioxide was filtered off
10. concentrationthe filtrate was concentrated under reduced pressure
11. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19, volume ratio)

ORD 기록

ord-2a6f4a266bc04f5a81b1ff9e704d25e5

출처 데이터셋

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08309580B2