Water → HCID 12893752, compound

Participants

Reaction Conditions

Reaction Steps

To the compound [VIII-2] (2.50 g) obtained above are added water (123.8 g) and acetic acid (0.19 g), and the pH value of the mixture is adjusted to pH 4.2 with 5% aqueous sodium hydroxide solution and the mixture is heated with stirring at 100° C. for 26 hours. After completion of the reaction, the reaction mixture is cooled and extracted twice with methyl isobutyl ketone (50 ml). The organic layer is separated and concentrated to give a mixture (1.78 g, yield; 71%) of 4-hydroxy-2-(6-methoxycarbonyl-cis-3-hexenyl)-2-cyclopentenone (racemic 4-hydroxycyclopentenone) and 3-hydroxy-2-(6-methoxycarbonyl-cis-3-hexenyl)-2-cyclopentenone [IX-2] (ratio thereof=4.9:5.1).

Provenance & Evidence