Acetic Acid → HCID 57741110, compound

Participants

Reaction Conditions

Reaction Steps

To a vigorously stirred solution of (1S,2R,3R,4S,5R,6R)-4-(acetoxymethyl)-6-(4-chloro-3-(4-ethylbenzyl)phenyl)cyclohexane-1,2,3,5-tetrayl tetraacetate (19) (300 mg, 48.7 μmol) in acetic acid (5 mL) was added K2Cr2O7 (172 mg, 0.58 mmol) and the mixture was stirred for 22 hours at 125° C. The mixture was cooled to room temperature, diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with saturated NaHCO3 (3×10 mL) and then with brine (20 mL), dried (Na2SO4), filtered and concentrated. Preparative TLC (2:1 hexane:ethyl acetate) afforded 100 mg of the desired compound. MS (ESI+): 631 [M+H]+, 648 [M+H2O]+.

Provenance & Evidence