Hydrochloric Acid → HCID 15840675, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-chloro-4-(3-(4-propyl-N-(4-chlorophenyl)-5-indoleoxy)propylthiophenyl-acetate (Step F; 100 mg, 0.18 mmol) was taken up in 3 mL methanol:water (2:1). To this was added a 0.5M solution of potassium hydroxide in methanol (1.80 mL, 0.90 mmol). The reaction was heated to 30° C. for 2 hours at which time the mixture was acidified to pH 3 with 1M hydrochloric acid. The aqueous solution was extracted with ethyl acetate and the organic layer was washed with water, brine, dried over magnesium sulfate, filtered, concentrated in vacuo, and the crude residue purified by flash chromatography on silica gel (30% ethyl acetate/hexane/1% acetic acid) to provide the title compound as a golden oil which solidifies upon pumping.

Provenance & Evidence