[H-].COCCO[Al+]OCCOC.[Na+].[H-].[O:15]1[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])[CH:16]1[CH2:17][OH:18].[OH-].[Na+]>O1CCCC1>[OH:18][CH2:17][CH2:16][C@@H:19]([OH:15])[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25]2 ml of a 3.4 molar solution sodium bis-(2-methoxyethoxy)-aluminum hydride (Red-AlR) (6.8 mM) are slowly added to a solution of 0.61 g (3.91 mM) 2S, 3S-2-epoxy-1-hydroxynon-8-ene (III) in 100 ml tetrahydrofuran at 0° C. in an argon gas atmosphere with agitation. After the addition, the mixture is allowed to react 3 hours at 0° C. and the reaction solution is subsequently left overnight at 25° C. After a careful addition of 5 ml 1 molar sodium hydroxide solution, the mixture is allowed to react one more hour with agitation. The organic phase is separated off and the aqueous phase is washed with 30 ml ether. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and subsequently the solvent is evaporated in a vacuum. Bulb tube distillation at 130° C./0.5 mm pressure yields 0.54 g (3.42 mM) 1,3(S)-dihydroxynon-8-ene (IV) with a melting point of approximately 20° C. This corresponds to a yield of 89%.
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