Sodium 3-carboxy-2,3-dihydroxypropanoate → 15-(3,17beta-Dihydroxyoestra-1,3,5(10)-trien-7alpha-yl)pentadecan-5-one

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Reaction Steps

n-Butyl-lithium (0.27 ml. of a 1.5 molar solution in diethyl ether) was added to a stirred solution of 11-(17β-acetoxy-3-hydroxyoestra-1,3,5(10)-trien-7α-yl)undecanoic acid (Example 2; 0.046 g.) in tetrahydrofuran (1 ml.) and the mixture was stirred at laboratory temperature for 2 hours. Saturated aqueous sodium hydrogen tartrate solution (2 ml.) was added and the mixture was extracted three times with ethyl acetate (5 ml. each time). The combined extracts were washed with water, dried and evaporated to dryness and the residue was purified by chromatography on a silica gel column using a 17:3 v/v mixture of toluene and ethyl acetate as eluant. There was thus obtained as an oil 15-(3,17β-dihydroxyoestra-1,3,5(10)-trien-7α-yl)pentadecan-5-one, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Provenance & Evidence