Methanol → HCID 13118020, compound

Participants

Reaction Steps

A solution of 1-(SR)-3-methylene-4-(SR)-phenylcyclopentanoic acid (84.8 g, 0.42 mol) from Example 20, Step B in methanol (2.5 L) was cooled to −70° C. in a dry-ice acetone bath. Ozone was bubbled through the solution until the blue color persisted. Excess ozone was removed with a stream of nitrogen and dimethyl sulfide (125 mL, 1.68 mol) was added. The mixture was then allowed to warm to rt over 16 h. Most of the methanol was removed in vacuo and the residue was taken up in ethyl acetate and washed twice with water and brine, dried over sodium sulfate and concentrated. The residue was triturated with hexanes and the solid was filtered and dried to afford the title compound (61.4 g).

Provenance & Evidence