m-Chloroperbenzoic acid → Methyl 7-[2-hydroxy-5-(3-hydroxy-1,2-epoxy-1-octyl)cyclopentyl]heptanoate

Participants

Reaction Steps

A solution of methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate (1.0 g.) [prepared as described in Example 5], metachlorperbenzoic acid (2.0 g.) and dichloromethane (30 ml.) was refluxed for days. The precipitated metachlorbenzoic acid was filtered from the cooled solution and washed with dichloromethane. The filtrate was washed successively with sodium sulphite solution, twice with 5% sodium bicarbonate solution and finally water, dried over sodium sulphate and evaporated to give methyl 7-[2-hydroxy-5-(3-hydroxy-1,2-epoxy-1-octyl)cyclopentyl]heptanoate (0.96 g.,92%), νmax 3450 cm-1, 1730 cm-1 and 1170 cm-1.

Provenance & Evidence