Hydrochloric Acid → HCID 19390049, compound

Participants

Reaction Steps

Sodium borohydride (0.400 g) was added in portions to a solution of 10.0 g of 3,9-dioxo-spiro[5.5]undecane (III) (Rice L. M. et al., J.Org.Chem., 1967, 32, 1966) in 80 ml of ethanol, under nitrogen atmosphere, at room temperature. After 1.5 hrs, 10.0 ml. of 1N hydrochloric acid were added and the resulting mixture was evaporated under reduced pressure. The crude residue, dissolved in 150 ml. of ethyl acetate, was washed with water to neutrality. The organic layer, dried over anhydrous sodium sulfate, was evaporated to dryness under reduced pressure to give a mixture of starting material, 3,9-dihydroxy- and 9-hydroxy-3-oxo-spiro[5.5]undecane. The components of the mixture were separated by flash chromatography (SiO2 ; ethyl acetate/n-hexane 70/30) and 2.80 g of 9-hydroxy-3-oxo-spiro[5.5]undecane were obtained as a white solid, mp 65°-67° C. TLC: Rf=0.32 (SiO2 plates, diethylether) 1H-NMR (300 MHz, CDCl3, ppm from TMS): 3.75 (1H, hept), 2.35 (4H, q), 1.25-1.95 (12H, m)

Provenance & Evidence