4-Ethoxy-3,3'-difluoro-4'-((4-propylcyclohexyl)methoxy)-[1,1'-biphenyl]-2,2'-dicarboaldehyde → 2-Ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)-9,10-di hydrophenanthrene-9,10-diol

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Reaction Steps

Under a nitrogen atmosphere, zinc powder (1.85 g, 28.30 mmol) and zinc chloride (0.64 g, 4.696 mmol) were added to a DMF (50 mL) solution of compound (63) (4.20 g, 9.449 mmol), and the resultant mixture was agitated at 80° C. for 8 hours. The reaction mixture was quenched with 100 mL of 1N hydrochloric acid aqueous solution, and extracted with 50 mL of toluene 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 purified by silica gel column chromatography, and thus 2-ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)-9,10-dihydrophenanthrene-9,10-diol (64) (3.6 g, yield 85.4%) was obtained.

Provenance & Evidence