HCID 58604052, compound → HCID 58604045, compound

Participants

Reaction Steps

Potassium hydroxide (8 g, 87% weight pure, 0.12 mol) was dissolved in 7:1 water-EtOH (80 mL) to give a 1.56M solution. A suspension of 2-butyl-5-methoxy-(2-oxopropyl)-1-indanone (83 mg, 0.3 mmol) in 5 mL of the KOH solution was stirred and heated at reflux for 23 hours. After cooling, the mixture was diluted with water (10 mL) and extracted with EtOAc (3×30 mL). The extracts were washed with 1N HCl, water, and brine (20 mL each), dried over MgSO4, filtered, and concentrated under vacuum to an oil. 1H NMR revealed a 65:35 mixture of desired product to starting material. The mixture was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.), developing twice with 5:1 hexane-EtOAc. The product band was extracted with EtOAc and the extracts evaporated under vacuum to provide 8a-butyl-6-methoxy-8,8a-dihydrocyclopenta[a]inden-2(1H)-one as an oil.

Provenance & Evidence