Cyclopentanone → HCID 13851033, compound

Participants

Reaction Steps

5,7-dihydroxyoctanoic acid delta-lactone was prepared in several steps from cyclopentanone and 2-benzyloxy-1-chloropropane. Thus, alkylation of cyclopentanone was effected by treatment with sodium hydride in tetrahydrofuran (THF) solution to generate the alpha-anion, followed by the dropwise addition of a THF solution of 2-benzyloxy-1-chloropropane. Reaction workup yielded 2-(2-benzyloxy-1-propyl) cyclopentanone. This ketone was treated with peroxy trifluoroacetic acid under Baeyer-Villiger conditions to give the 7-benzyl ether of 5,7-dihydroxyoctanoic acid gamma-lactone. The benzyl group was removed by catalytic hydrogenation, yielding 5,7-dihydroxyoctanoic acid delta-lactone.

Provenance & Evidence