Water → HCID 53711472, compound

Participants

Reaction Steps

Sodium chlorite (53 mg, 0.6 mmol) was added to a mixture of 17β-(5,5,5-trifluoro-1-oxopentyl)-androsta-3,5-diene-3-carboxaldehyde (50 mg, 0.12 mmol), sodium phosphate, monobasic monohydrate (140 mg, 1.18 mmol) in 2-methyl-2-butene in THF (2.0M, 3.0 ml), H2O (0.5 mL), and t-butanol (0.5 ml) at RT. After 6 h acetic acid (3.0 mL) was added, then the aqueous layer was extracted with EtOAc (10 mL), the combined organic extracts were dried (MgSO4), filtered, concentrated, and flash chromatographed (silica gel, 1% AcOH/19% EtOAc/80% hexanes) to yield the title compound as a white waxy solid. ESMS m/e 439 [M+H]+

Provenance & Evidence