2-Ethoxy-1,8-difluoro-7-propyl-9,10-dihydrophenanthrene-9,10-diol → 2-Ethoxy-1,8-difluoro-7-propylphenanthrene-9,10-dione

Participants

Reaction Steps

IBX (31.5 g, 112.5 mmol) was added to 100 mL of DMSO, and the resultant mixture was agitated at room temperature for 30 minutes, and then compound (57) (9.4 g, 28.11 mmol) was added and the resultant mixture was further agitated for 3 hours. The reaction mixture was filtered, 200 mL of water was added to a filtrate, and the resultant mixture was extracted with 100 mL of ethyl acetate three times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was recrystallized from toluene, and thus 2-ethoxy-1,8-difluoro-7-propylphenanthrene-9,10-dione (58) (3.2 g, yield 34.5%) was obtained.

Provenance & Evidence