Ammonium Chloride → 7-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one

Participants

Reaction Conditions

Reaction Steps

7-Bromo-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one (0.14 g) was suspended in THF (6 mL) and dissolved by heating. This solution was cooled to −70° C. and a solution (1.6 M: 0.75 mL) of n-butyllithium in hexane was slowly added dropwise. After stirring for 1 hr., a solution (1 mL) of 2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanone (0.16 g) in THF was added dropwise. After stirring at −70° C. for 30 min., 20% aqueous ammonium chloride was added to stop the reaction. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (carrier: silica gel, developing solvent: hexane-ethyl acetate, 1:1—ethyl acetate) to give the title compound (0.13 g) as colorless crystals.

Provenance & Evidence