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To a solution of 5-chloroindanone (10 g) and dimethyl carbonate (6.0 ml) in THF (80 ml) was added a 60% oil dispersion (5.0 g) of sodium hydride at room temperature, followed by heating at reflux for 12 hours. After cooling to room temperature, methyl iodide (5.0 ml) was added thereto, and the mixture was heated again at reflux for 12 hours. The reaction mixture was poured into ice-water and extracted with dichloromethane (300 ml×3). The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to chromatography on silica gel to give methyl 5-chloro-2,3-dihydro-2-mehtyl-1-oxo-1H-indene-2-carboxylate (yield, 5.3 g).

1. temperatureby heating
2. temperatureat reflux for 12 hours
3. temperaturethe mixture was heated again
4. temperatureat reflux for 12 hours
5. extractionextracted with dichloromethane (300 ml×3)
6. dry with materialThe extract was dried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure