Water → HCID 70153490, compound

Participants

Reaction Conditions

Reaction Steps

Excess Jones reagent (5.0 ml) prepared by a slow addition of concentrated sulfuric acid (150 ml) to a cold solution (0-5° C.) of CrO3 (180 g, 1.8M) in ice water (1.21) and stirred for one hour at 0° C., was slowly added to a cold mixture of Compound 17 as prepared in Example 3 (4.0 g, 7.8 mM) in acetone (60 ml). The resulting mixture was stirred at room temperature overnight. Water (100 ml) was then slowly added and the volatile solvents removed in vacuo. The aqueous mixture was extracted with ethyl acetate (2×100 ml). The combined EtOAc extracts were dried (MgSO4), filtered and evaporated in vacuo to give a crude product. Purification by flash column chromatography (EM silica gel 60; 10% EtOAc in CH2Cl2) gave the desired product as a white solid. m/z (MH+) 539.

Provenance & Evidence