Water → HCID 11518518, compound

Participants

Reaction Conditions

Reaction Steps

As depicted in Scheme 34 below, Compound 43 (30 mg, 0.2 mmol) was dissolved in dry acetonitrile (2 ml), under nitrogen atmosphere, and the solution was cooled to −10° C. Nitrosyltetrafluoroborate (NOBF4, 28 mg, 0.24 mmol) in dry acetonitrile (1 ml) was then added and the resulting mixture immediately turned red. The mixture was stirred for one hour at −10° C., and a mixture of 2-(4-nitrophenyl) furan (75 mg, 0.4 mmol) and CuCl2 dihydrate (5 mg) in acetonitrile (1 ml) was thereafter added dropwise. The resulting mixture was allowed to warm to 0° C., and stirring was continues while monitoring the reaction by TLC. Once the reaction was completed (after about one hour), a mixture of ethyl acetate and water was added, and after separation of the phases the organic phase was dried over Na2SO4, and the solvent was evaporated under reduced pressure to give 130 mg of the crude red product. Purification by column chromatography using fine silica and a 4:1 hexane:ethyl acetate mixture as eluent gave 16 mg of Compound 45 as a red oily solid (15-20% yield). The product was further purified by preparative HPLC using an acetonitrile:water gradient as a mobile phase.

Provenance & Evidence