Water → HCID 86646399, compound

Temperature

0 °C

Methyl 4-methyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylate (3.0 g) synthesized above was dissolved in tetrahydrofuran (10 mL) and added dropwise to a solution (15 mL) of lithium aluminum hydride (0.40 g) in tetrahydrofuran at 0° C. The reaction mixture was stirred at 0° C. for 30 min, water (0.40 mL) was carefully added dropwise, 1N aqueous sodium hydroxide solution (2.0 mL) was added, and the mixture was stirred at room temperature for 30 min. The reaction mixture was filtered through celite, and the residue was washed with tetrahydrofuran (30 mL). The extracts were combined, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in toluene (50 mL), manganese dioxide (6.0 g) was added, and the mixture was heated under reflux under dehydrating conditions for 1 hr. After cooling, manganese dioxide was filtered off, and the residue was evaporated under reduced pressure to give the title compound (2.3 g, 86%) as a slightly yellow solid.

1. stirringthe mixture was stirred at room temperature for 30 min
2. filtrationThe reaction mixture was filtered through celite
3. washthe residue was washed with tetrahydrofuran (30 mL)
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in toluene (50 mL)
7. additionmanganese dioxide (6.0 g) was added
8. temperaturethe mixture was heated
9. temperatureunder reflux under dehydrating conditions for 1 hr
10. temperatureAfter cooling
11. filtrationmanganese dioxide was filtered off
12. customthe residue was evaporated under reduced pressure

ORD record

ord-b1d46c4fd64b456e9ceb6c2b8a2f9ad3

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309580B2