1,4-Dioxane → HCID 68992721, compound

Participants

Reaction Steps

A solution of Example 173B (150 mg, 0.35 mmol) in dioxane (6 mL) and water (2 mL) was added OSO4 (2.5% wt in t-butanol, 0.5 mL) was stirred for 8 minutes at ambient temperature, treated with NaIO4 (128 mg, 0.6 mmol), stirred for 30 minutes, treated with brine, and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated. The concentrate was dissolved in anhydrous THF (6 mL), cooled to 0° C., treated dropwise with methyl magnesium bromide (3.0M in diethyl ether, 0.37 mL), treated with water (20 mL) and 1N HCl (1.0 mL), and extracted with ethyl acetate (2×20 mL). The ethyl acetate solution was dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography on silica gel with 40% ethyl acetate/hexanes to provide the desired product.

Provenance & Evidence