Hydrochloric Acid → HCID 9965857, compound

Participants

Reaction Conditions

Reaction Steps

4.7 g (0.019 mol) of 4-(3,4-dimethoxyphenyl)-4-oxo-butanoic acid (FN 549) are dissolved in 50 ml of 47% HBr in water, heating to reflux for one hour until the reaction compound disappears. The reaction solution is concentrated to dryness, adding acetonitrile several times, and then the dark pitch is extracted hot several times with ethyl ether. On concentrating the organic solution to dryness, 3.3 g of crude product are obtained, which can be used as such in the next reaction. 3.3 g (0.015 mol) of crude 4-(3-hydroxy-4-methoxyphenyl)-4-oxo-butanoic acid (FN 551) are suspended in 30 ml of anhydrous DMF with 6.2 g (0.045 mol) of K2CO3, left under stirring for 30 minutes, and then added with 2.4 ml (0.0225 mol) of bromocyclopentane and heated at 70° C. for 4 hours under a nitrogen atmosphere. After one night at room temperature, the reaction mixture is dried under reduced pressure and the residue obtained is divided between HCl 2N and EtOAc, washing the organic phase with water. The reaction mixture is anhydrified on anhydrous sodium sulphate and evaporated to dryness, obtaining a dark oil which is chromatographed on a silica gel column, eluting with n-hexane/EtOAc. After crystallisation, the same mixture of solvents yields fractions containing the dried product. 0.63 g of product are obtained. Yield 14%.

Provenance & Evidence