Sodium ethoxide → Coumaranone

Participants

Reaction Steps

To a stirred solution of 1.0 g (4.2 mmol) of the title compound from Step B in 30 ml toluene was added 2.9 g (9.2 mmol) of 21% sodium ethoxide. The reaction was refluxed overnight. After cooling down to RT, the reaction was filtered and the solid was collected. The solid was then dissolved in 20 ml water, and acidified by acetic acid. The solid was filtered and washed with dichloromethane and dried. The solid was added to 30 ml of 10% HCl aqueous solution and refluxed for 3 hr. Then HCl was evaporated to give 350 mg (62% yield) of the title compound. LC/MS: (M+1) 136.1

Provenance & Evidence