Sodium borohydride → HCID 53819009, compound

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Reaction Conditions

Reaction Steps

A solution of 100 mg of 2-[3-(2,5-dihydro-2-methoxy-5-oxo-3-furanyl)propylidene]-6,10-dimethyl-5,9-undecadienal (Example 15G) and 10.9 mg of sodium borohydride in 30 ml of dry methanol under an argon atmosphere was stirred for four hours at room temperature followed by four hours of stirring at 35° C. The reaction was quenched by the slow addition of water and the mixture was extracted with ether. The organic layer was washed with water and a saturated sodium chloride solution, dried over magnesium sulfate and evaporated in vacuo. The residue was dissolved in 3 ml of tetrahydrofuran and 0.34 ml of 0.1N sodium hydroxide at room temperature and under argon. The solution was brought to reflux for two hours, cooled, and adjusted to pH 4 with the slow addition of 0.1N hydrochloric acid. Extraction with ether provided an organic solution which was washed with 0.01N hydrochloric acid and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The resulting oil was purified by medium pressure liquid chromatography over silica gel eluting with 1:2 hexane/ethyl acetate to afford 56.8 mg of the title product as an oil. Proton NMR, 13C NMR, and mass spectra were consistent with the desired structure.

Provenance & Evidence