Acetic Acid → HCID 131731401, compound

Participants

Reaction Conditions

Reaction Steps

cis-Ethyl 6-chloro-3a-methyl-3,3a,4,5-tetrahydro-1H-benzo[e]isoindole-2(9bH)-carboxylate (5.55 mmol, 1630 mg) was dissolved in water (33 ml), acetic acid (8.25 ml) and 1,4-dioxane (8.25 ml). Cerium(IV) oxide (1.276 mmol, 220 mg) and sodium bromate (5.55 mmol, 837 mg) were added and the reaction mixture was heated to 95° C. for 3 hours. The reaction mixture was cooled to rt, diluted with water (30 ml) and extracted with ether. The organic extracts were dried over magnesium sulphate, filtered and the solvent removed in vacuo to give to give a crude residue that was purified by silica column chromatography (eluting with 0-60% ethyl acetate in heptane) to give cis-ethyl 6-chloro-3a-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-benzo[e]isoindole-2(9bH)-carboxylate (673 mg), m/z=308.7 [M+H]+.

Provenance & Evidence