Ammonium Chloride → 4-(1-ethyl-1-{4-[(E)-2-(1-hydroxy-cyclohexyl)-vinyl]-3-methyl-phenyl}-propyl)-2-methyl-phenol

Participants

Reaction Steps

4-{1-Ethyl-1-[4-(1-hydroxy-cyclohexylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol (Example 35-(1); 0.2 g, 0.51 mmol) was added to a solution of lithium aluminum hydride (38.9 mg, 1.02 mmol) in tetrahydrofuran (2 mL), and the mixture was stirred for five hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (20% ethyl acetate/hexane) to give the title compound (0.17 g, 88%).

Provenance & Evidence