Ammonium Chloride → HCID 15518231, compound

Participants

Reaction Steps

In a dry flask, a piece of magnesium (0.468 g, 19.3 mmols) was charged, and tetrahydrofuran (15 mL) was added thereto. A solution of 3-(t-butyldimethylsiloxy)propyl bromide (2.36 g, 9.63 mmols) in tetrahydrofuran (15 mL), iodine (a few pieces) and 1,2-dibromoethane (a few drops) were added portionwise to the mixture. The resulting mixture was stirred at room temperature for an hour. A solution of 2,3-(methylenedioxy)-5-methyl-6-ethoxy-7-benzyloxy-8-methoxy-5,6-dihydrobenzo[c]phenanthridine (1.01 g, 2,2 mmols) in tetrahydrofuran (10 mL) was added to the resulting solution followed by stirring at room temperature for 2 hours. A saturated ammonium chloride aqueous solution was added to the reaction mixture followed by extracting with ethyl acetate. The organic layer was separated, washed with saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. After sodium sulfate was removed by filtration, the solvent was distilled off in vacuo. The resulting residue was purified by silica gel column chromatography (eluted with 33-66% methylene chloride-hexane) to give 2,3-(methylenedioxy)-5-methyl-6-[3-(t-butyldimethylsiloxy)propyl]-7-benzyloxy-8-methoxy-5,6-dihydrobenzo[c]phenanthridine (1.12 g, yield 96%) as colorless amorphous solid.

Provenance & Evidence