HCID 13621740, compound → HCID 13621746, compound

Participants

Reaction Steps

A solution of XIII (6.6 g, 0.035 mole) in glacial HOAc (40 mL) and 48% HBr (110 mL) was stirred at reflux for 7 hours and then evaporated to dryness in vacuo. The residue was stirred with saturated NaHCO3 (200 mL) for 16 hours at room temperature. The aqueous phase was decanted from the residue which again was stirred with saturated NaHCO3 for 2 hours. This aqueous phase was decanted and the residue was extracted with 3×100 mL of boiling H2O filtering from insoluble material. All of the aqueous phases were combined and evaporated to dryness in vacuo. The residue was extracted with 3×100 mL of CHCl3 --MeOH (60:40), filtering from inorganic material. Evaporation of the filtrate left the crude product as an oily brown solid that was purified by chromatography on silica gel, eluting with 90CHCl3 --10MeOH--1H2O; to yield XIV (74%); m.p. 188°-190° C. (CH3CN).

Provenance & Evidence