Borane;tetrahydrofuran → HCID 18408982, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of 7-4 (31.3 g, 198 mmol) in 200 mL anhydrous THF was added borane-THF solution (1.5M, 660 mL, 990 mol). The reaction mixture was stirred at room temperature overnight. It was then quenched with methanol gradually until no gas was released. Then additional methanol (150 ml) was added, followed by 30 mL of 6N HCl. The mixture was stirred for 1 hr and concentrated to a viscous residue. It was then treated with 6N NaOH until pH >11 and stirred for 30 min and extracted four times with CHCl3. After solvent removal, the residue was purified using silica gel chromatography (100%EtOAc to 50% EtOAc/46% EtOH/2% NH4OH/2% H2O) to obtain the desired product 7-5 as an oil.

Provenance & Evidence