Reaktion #1700180

Reaktionsgleichung

methyl isobutyl ketone

water

racemic 4-hydroxycyclopentenone

chloral

triethylamine

→

4-hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone

racemic 4-hydroxycyclopentenone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter completion of the reaction
2. 2
   Sonstigethe organic layer is separated
3. 3
   Waschenwashed successively with 1% aqueous hydrochloric acid solution and water, and methyl isobutyl ketone
4. 4
   workup.DISTILLATIONis distilled off

Vorschrift

A mixture of the mixture (9.45 g) of the compound [IX-1] and the racemic 4-hydroxycyclopentenone obtained in Example 13, chloral (0.24 g) and triethylamine (0.43 g) is reacted at 60° C. for 5 hours. After completion of the reaction, to the mixture are added methyl isobutyl ketone (30 ml) and water (20 ml), and the organic layer is separated, washed successively with 1% aqueous hydrochloric acid solution and water, and methyl isobutyl ketone is distilled off therefrom to give 4-hydroxy-2-(6-methoxycarbonyl-3-hexynyl)-2-cyclopentenone [racemic 4-hydroxycyclopentenone) (8.13 g, yield; 86%).

Quelle