The pentane solution was poured into ice-cold, saturated, aqueous NH4C1, after which 25 mL of 12 M aqueous H2S04 was added. The layers were separated, and the aqueous layer was washed with pentane. The organic layers were combined, dried with Na2S04, and rotary evaporated. The major product, 9-ethyl-cis-2-decalone (19),20 was collected by thin-layer chromatography (hexane): IR (CC14) 1715 cm'1 (C=0);
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