Water → HCID 22267208, compound

Participants

Reaction Steps

A solution of (6-hydroxy-2,3-dihydro-1H-inden-5-yl)(2-methylphenyl)methanone (2.0 g) in DMF (50 ml) was combined with sodium hydride (60%, in oil) (400 mg) with cooling in ice. After stirring at the same temperature for 30 minutes, the mixture was combined with ethyl bromoacetate (1 ml), and stirred for 1 hour. The reaction solution was combined with water and extracted with ethyl acetate. The extract was washed with water, and then dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was dissolved in toluene (50 ml), and combined with DBU (2 ml). The reaction solution was heated under reflux overnight, and then combined with water, and extracted with ethyl acetate. The extract was washed with water, and then dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by a column chromatography (packing: silica gel, eluent: ethyl acetate-hexane=1:3) to obtain a crude product of ethyl 3-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]furan-2-carboxylate. The resultant crude product of ester was dissolved in a solvent mixture of THF (50 ml) and methanol (30 ml), combined with a 1 N solution of sodium hydroxide (30 ml), and stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and the resultant residue was combined with water and extracted with ethyl acetate after acidifying with diluted hydrochloric acid. The extract was washed with water, and then dried over magnesium, and the solvent was distilled off under reduced pressure. The resultant residue was purified by recrystallization from ethyl acetate to obtain the title compound (0.9 g, yield: 39%) as a colorless crystal.

Provenance & Evidence