Hydrogen Peroxide → HCID 59649298, compound

Participants

Reaction Steps

Into a clean flame dried 1 L RBF under current of N2, was put 12.86 g (34.48 mmol) of 54. To this was added 172 mL (86.2 mmol) of 9-BBN (0.5 M in THF). The reaction was stirred for 3 h. 23 mL of 30% H2O2 was then added dropwise to the reaction mixture followed by 49 mL of 15% aq. NaOH and the reaction mixture was stirred at 85° C. for 3 h. The mixture was then cooled to room temperature and THF was evaporated and the residue was diluted with H2O and extracted with EtOAc (3×). The combined organic layer was then washed with brine (1×), dried over MgSO4, filtered and the solvent was evaporated under vacuum. The residue was then purified using combiflash (120 g silica column) with hexane/ethyl acetate as eluent to furnish 10.15 g (76%) of compound 55 as a white solid.

Provenance & Evidence