Ammonium cerous sulfate → HCID 19390019, compound

Participants

Reaction Conditions

Reaction Steps

9-Hydroxy-3-hydroxymethyl-spiro[5.5]undecane (0.29 g) and ammonium cerium sulfate (0.830 g) were added to a suspension of sodium bromate (0.230 g ) in acetonitrile and water (9 ml; 70:30). The mixture was heated at 80 ° C. for 3 hrs, cooled to 0 ° C., and treated with sodium bicarbonate to neutral pH. After evaporation under reduced pressure to small volume and extraction with ethyl acetate, the organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure to give 0.220 g of a crude residue, that was purified by flash-chromatography (SiO2 ; ethyl acetate/n-hexane 60/40) to give 0.200 g of 9-hydroxymethyl-3-oxo-spiro[5.5]undecane (II-d) a light oil. TLC: Rf=0.35 (SiO2 plates, ethyl acetate/n-hexane 60/40). 1H-NMR (300 MHz, CDCl3, ppm from TMS): 3.50 (2H, d), 2.36 (2H, t), 2.28 (2H, t), 1.85-1.09 (13H, m).

Provenance & Evidence