Acetic Acid → HCID 53967837, compound

Participants

Reaction Steps

A solution of approximately 7.25 mmol of 5,6,7,8-tetrahydro-9-[(4-fluorophenyl)methyl]-9H-dibenzo[b,d]pyrrol-3-ol as a crude oil from Example 100 in 20 ml of dimethyl sulfoxide was added dropwise to a freshly prepared suspention of 0.35 g of sodium hydride (55% dispersion in mineral oil) in 2 ml dimethylsulfoxide at room temperature and under argon. The resulting mixture was stirred an additional 15 minutes and a solution of methyl 5-nitro-2-furoate (1.37 g) in dimethylsulfoxide (10 mL) was added. The black mixture was stirred an additional 2 hours and poured into ice and water containing a few drops of acetic acid. The product was extracted with dichloromethane and the organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by HPLC eluting with ethyl acetate-hexane (1:9) and crystallized from ether-hexane. 2.2 g (72%) of 1,2,3,4-tetrahydro-5-[[9-[(4-fluorophenyl)methyl]-9H-dibenzo[b,d]pyrrol-6-yl]oxy] -2-furancarboxylic acid methyl ester was obtained as a colorless crystalline material, mp 85°-86° C.

Provenance & Evidence