Methane → HCID 131715725, compound

Participants

Reaction Steps

To a suspension of [(2-cyclopentyl-6,7-dichloro-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy]acetonitrile (3.88 g, 10 mmole; see Example 1) in methanol (50 ml) was added sodium metal (0.1 g, 4 mg-atom), and the mixture was stirred for one hour. Ammonium chloride (0.6 g, 11 mmole) was added and the mixture was stirred overnight. The mixture was concentrated to dryness in vacuo, and the resultant residue was triturated with boiling benzene, then collected by filtration. The solid was dissolved in a minimum amount of dimethylformamide and filtered. The filtrate was diluted with diethyl ether (100 ml), giving an oil from which the ether supernatant was removed by decanting. Trituration with warm benzene gave a solid. The ether than was removed by decanting produced an additional quantity of the oil, which solidified on standing. The solids were combined and dissolved in boiling dioxane (50 ml). The cloudy solution was decolorized with charcoal, filtered, and diluted with benzene to yield a white solid. Drying at 80° at 1 mm Hg pressure produced the title compound (ca. 1.7 g) as an analytically pure solid.

Provenance & Evidence