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Alkene to Aldehyde

(OsO4 + NaIO4)


Example 1

The SM (1.03 g, 3.58 mmol), NaIO4 (2.34 g, 10.9 mmol), OsO4 (2.5 wt% in t-BuOH, 1.0 mL), THF (12.4 mL), and H2O (2.4 mL) were combined at RT. The reaction mixture was stirred overnight in the dark, after which time it was diluted with H2O and DCM. The layers were separated using a hydrophobic frit. The org layer was dried (Na2SO4) and concentrated. The residue was purified by silica gel flash chromatography to provide the product as an amber oil. [786 mg, 76%]

[Patent Reference: WO2016014463, page 98, (6.7 MB)]

Example 2

The SM (200 mg, 0.84 mmol) was combined with NaIO4 (737 mg, 3.45 mmol) and OsO4 (polymer bound, 292 mg, 0.057 mmol) in dioxane (3 mL) and H2O (1 mL). The reaction mixture was stirred at RT overnight. The mixture was diluted with EtOAc (5 mL) and H2O (5 mL). The mixture was filtered through glass wool and the layers were separated. The org layer was dried (MgSO4) and concentrated to provide the crude product which was used without further purification. [40 mg, 20%]

[Patent Reference: WO2015069512, page 16 (2.6 MB)]