Sodium Dithionite → HCID 10420440, compound

Participants

Reaction Steps

To a solution of 2,2-dimethyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine (50 mg, 0.29 mmol) in 4.5 mL of THF-tert-BuOH—H2O (1:3:0.5) was added NMO (45 mg, 0.32 mmol) and the solution was stirred for 5 min at ambient temperature. OsO4 (15 μL, 25 wt % in tert-BuOH) was added and the solution was stirred at ambient temperature for 4 days. Sodium hydrosulphite (0.2 g), Florisil (2.0 g) and H2O (5 ml) were added and the mixture was stirred for 30 minutes, wash with acetone (100 mL), filtered through filter paper and extracted with EtOAc (80 mL×2). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, concentrated in vacuo, and the residue was purified by flash chromatography with 60% EtOAc-hexane.

Provenance & Evidence