1-Indanone → 7-Nitro-chroman-2-one

Participants

Reaction Steps

6-Nitroindanone [J. Med. Chem., 19, 1976, 472–475] (900 mg, 5.0 mmol) was suspended in dichloromethane (25 ml) and trifluoromethanesulphonic acid (0.05 ml) added. The resulting solution was cooled on ice. In a second flask, m-chloroperoxybenzoic acid [55%, Aldrich] (10 g) was suspended in dichloromethane and stirred for several minutes. The insoluble material was removed by filtration through a hydrophobic membrane and the filtrate evaporated to give a white powder. A portion of this material (2.6 g) was added portionwise to the indanone and the resultant suspension stirred for 72 h at room temperature. The reaction mixture was diluted with dichloromethane (10 ml) and aqueous sodium disulphite (20%; 10 ml). The aqueous layer was extracted (30 ml×3) with dichloromethane and the combined organic layers washed with saturated aqueous sodium bicarbonate (20 ml), brine (10 ml), and dried (MgSO4) to yield crude 7-nitro-chroman-2-one as a brown solid (1.1 g, ˜70% pure);

Provenance & Evidence