Water → 5-(1,3-Dioxolan-2-yl)-2-ethylthiophene-3-carbaldehyde

To a solution of ethyl 5-(1,3-dioxolan-2-yl)-2-ethylthiophene-3-carboxylate (8.71 g) synthesized above in tetrahydrofuran (170 mL) was added lithium aluminum hydride (2.58 g) at 0° C., and the mixture was stirred for 1 hr. Water (5.20 mL) was added to quench the reaction, 1N aqueous sodium hydroxide solution (5.20 mL) was added, and the mixture was stirred at room temperature for 1 hr. The resulting insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give a colorless oil. To a solution of the obtained oil in tetrahydrofuran (150 mL) was added activated manganese dioxide (36.0 g), and the mixture was stirred at room temperature for 4.5 hr. Manganese dioxide was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (6.36 g, 88%) as a yellow oil.

1. customto quench
2. customthe reaction, 1N aqueous sodium hydroxide solution (5.20 mL)
3. additionwas added
4. stirringthe mixture was stirred at room temperature for 1 hr
5. filtrationThe resulting insoluble material was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. customto give a colorless oil
8. stirringthe mixture was stirred at room temperature for 4.5 hr
9. filtrationManganese dioxide was filtered off
10. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-8437ab8f44c34e53a43f661fa92b586c

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309580B2