Water → HCID 36995608, compound

To a solution (40 mL) of methyl 5-(trifluoromethyl)-1-benzothiophene-2-carboxylate (2.00 g) in tetrahydrofuran was added lithium aluminum hydride (292 mg) at 0° C., and the mixture was stirred for 1 hr. Water (300 μL) was added to quench the reaction, 1N aqueous sodium hydroxide solution (300 μL) was added, and the mixture was stirred at room temperature for 3 hr. The resulting insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give a white solid. To a solution of the obtained solid in tetrahydrofuran (40 mL) was added active manganese dioxide (9.00 g), and the mixture was stirred overnight at room temperature. Manganese dioxide was filtered off, and the filtrate was concentrated under reduced pressure to give the title object compound (1.15 g, 65%) as a brown solid.

1. customto quench
2. customthe reaction, 1N aqueous sodium hydroxide solution (300 μL)
3. additionwas added
4. stirringthe mixture was stirred at room temperature for 3 hr
5. filtrationThe resulting insoluble material was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. customto give a white solid
8. stirringthe mixture was stirred overnight at room temperature
9. filtrationManganese dioxide was filtered off
10. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-a7402650d96f42f48dcd707d253c05c1

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2