Water → 7-[2-(3-Hydroxy-3-methyloct-1-enyl)-5-oxocyclopentyl]heptanol

Participants

Reaction Steps

7-(3-Hydroxy-3-methyloct-1-enyl)-6-(7-trimethylsiloxyheptyl)-1,4-dioxaspiro[4,4]nonane [0.5 g; prepared as hereinbefore described in Example 3(iii)], water (10 ml.) and glacial acetic acid (20 ml.) were left to stand together at room temperature for 6 hours. The solution was then evaporated in vacuo at a temperature below 50° C. Ethyl acetate (150 ml.) was added to the residue and the resulting solution was washed with water until the pH of the washings was 5, dried over sodium sulphate, and evaporated to give a crude product (0.37 g.). The crude product was subjected to preparative thin layer chromatrography on silica gel, using a mixture of toluene, dioxan and acetic acid (65:15:1 by volume) as eluant, eluting twice, to give 7-[2-(3-hydroxy-3-methyloct-1-enyl)-5-oxocyclopentyl]heptanol (0.12 g.).

Provenance & Evidence