Sodium Bicarbonate → HCID 90060287, compound

Participants

Reaction Conditions

Reaction Steps

8-[2-(4-Phenyl-butyl)-[1,3]dioxolan-2-yl]-octan-1-ol (830 mg, 2.48 mmol) was dissolved in toluene (4.2 mL), and 4-acetamide-2,2,6,6-tetramethylpiperidine 1-oxyl (2.6 mg, 0.0122 mmol) and an aqueous solution of 5% sodium bicarbonate (4.2 mL, 2.50 mmol) were then added. The mixture was then cooled to 0° C. An aqueous solution of 12% sodium hypochlorite (1.55 mL, 2.50 mmol) was added over 15 minutes. The mixture was then stirred at room temperature for 3 hours, and extracted twice with ethyl acetate (50 mL). The organic layer was then concentrated under reduced pressure. The residue was purified on Biotage (diol, n-hexane/ethyl acetate) to obtain 528 mg of the title compound (1.59 mmol, 64% yield).

Provenance & Evidence