Isopropanol → HCID 86738048, compound

Participants

Reaction Steps

0.45 g of 1[4(3-hydroxy-1(1,3-dioxa-2-cyclohexyl)butyl]-2(3-tetrahydropyranyloxy-1-octenyl)-3(tetrahydropyranyloxy)-5-hydroxy-cyclopentane (IV) (Example 3) were dissolved in 30 ml of acetone. At -20° to -25° C., 2 ml of Jones reagent (2.1 g of chromic acid, 6 ml of water, 1.7 ml of concentrated sulfuric acid) were added under argon. The mixture was stirred for 30 minutes, 3 ml of isopropanol were added and stirring was continued for a further 10 minutes to destroy the oxidation reagent in excess. Next, 100 ml of methylene chloride and 100 ml of water were added, the mixture was shaken and the phases were separated. The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure at a temperature of at most +5° C. 0.32 g of compound VIII in the form of an almost colorless clear oil was obtained.

Provenance & Evidence