Water → HCID 20253406, compound

Participants

Reaction Steps

Chromium trioxide (12.0 g, 120 mmol) was dissolved in 120 mL of 3.5M H2SO4 (420 mmol) and cooled to -5°. A solution of diol 11 (4.30 g, 22.2 mmol) in acetone (250 mL) was added dropwise over 4 hr. When the addition was complete, the mixture was warmed to 20° over 45 min, then poured into water (400 mL), and extracted with ether (4×150 mL). The combined ether extracts were washed with brine (3×50 mL), dried (MgSO4), and concentrated in vacuo. The crude product was flash chromatographed9 (hexane:EtOAc:AcOH, 75:75:1), yielding 1.83 g (40% yield) of a highly unstable yellow oil.

Provenance & Evidence