Sodium Hydroxide → HCID 178461290, compound

Temperature

0 °C

Lithium aluminum hydride (0.35 g) was suspended in tetrahydrofuran (10 mL). To the suspension, a solution of the compound (1.67 g) obtained in Step 1 of this Reference Example in tetrahydrofuran (10 mL) was added dropwise under ice cooling. The mixture was stirred at 0° C. for 30 minutes and then at room temperature for 2 hours and 40 minutes, and water (2 mL), 5 N aqueous sodium hydroxide (2 mL), and water (6 mL) were added thereto in this order under cooling. The mixture was stirred at room temperature for 2 hours. Then, anhydrous sodium sulfate was added thereto, and the mixture was filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was dissolved in methylene chloride (20 mL). To the solution, manganese dioxide (21.6 g) was added, and the mixture was stirred at room temperature for 17 hours and then filtered through celite. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=50/50-20/80) to obtain the title compound (0.79 g).

1. waitat room temperature for 2 hours
2. temperaturein this order under cooling
3. stirringThe mixture was stirred at room temperature for 2 hours
4. filtrationthe mixture was filtered
5. concentrationThe filtrate was concentrated under reduced pressure
6. dissolutionthe obtained residue was dissolved in methylene chloride (20 mL)
7. additionTo the solution, manganese dioxide (21.6 g) was added
8. stirringthe mixture was stirred at room temperature for 17 hours
9. filtrationfiltered through celite
10. concentrationThe filtrate was concentrated under reduced pressure
11. customThe obtained residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=50/50-20/80)

ORD record

ord-bcae7a8c6f7e418e9fc835a4123ea03c

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609710B2