HCID 70199009, compound → HCID 53926227, compound

Participants

Reaction Steps

A solution of 2-(3-carboxypropyl)-7-nitrobenzo[b]furan (500 mg) in thionyl chloride (5 ml) was refluxed for 1.5 hours. The reaction mixture was diluted with toluene and concentrated in vacuo. The residue was dissolved in dichloromethane (15 ml) and to the mixture was added aluminum chloride (435 mg) at 4° C. The mixture was stirred at ambient temperature for 2 hours and partitioned between 1N-hydrochloric acid and dichloromethane. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from a mixture of ethyl acetate and n-hexane to give 6-nitro-1-oxo-1,2,3,4-tetrahydrodibenzofuran (282 mg).

Provenance & Evidence