1-Indanone → Methyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate

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Reaction Steps

The reaction is carried out according to J. Med. Chem., 1970, 650. A suspension of 6.75 g of sodium hydride at 80% in oil and 45 g of methyl carbonate in 120 ml of benzene are mixed together. 11.9 g of 1-indanone dissolved in 100 ml of benzene are added, at 60° C., over 1 and a half hours and the mixture is then refluxed. After 1 hour, the benzene is distilled off. Xylene is added and the mixture is again refluxed. After 1 hour, it is cooled, 30 ml of AcOH are added and the resulting mixture is poured onto 200 ml of a water/ ice mixture containing 30 ml of 1N HCl. The insoluble material is removed by filtration and the filtrate is extracted with Et2O. The extracts are washed with water, with saturated NaHCO3 solution, with water, with saturated NaCl solution and then dried over Na2SO4. The product is chromatographed on silica, eluting with EtOAc/hexane (1.3; v/v) in order to obtain 3.05 g of the expected compound.

Provenance & Evidence