Hydrochloric Acid → HCID 21401649, compound

Participants

Reaction Steps

A stirred suspension of sodium hydride (57%) (.91 g., 0.022 mole) in a solvent mixture of benzene (50 ml.) and dimethylformamide (50 ml.) is treated, over 30 minutes, with N-[4-acetoxy-5-(4-fluorophenoxy)pentyl] -methanesulfonamide (6.5 g., 0.02 mole). This mixture is heated at 60° C. until evolution of hydrogen ceases, then cooled to room temperature. At this temperature is added methyl 7-bromo-5-heptynoate (4.3 g., 0.02 mole) and the reaction is heated at 90° C. for 3 hours. The reaction is poured into water (200 ml.), neutralized with hydrochloric acid and extracted with ethyl acetate (2 × 100 ml.). The ethyl acetate layer is washed with brine, dried over sodium sulfate, then concentrated in vacuo. The product is purified by chromatography over silica gel using 5% methanol in chloroform to elute. Evaporation of the appropriate fractions affords the subject compound as a yellow oil.

Provenance & Evidence