Sodium Hydroxide → HCID 178461290, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence