Water → 4-{1-Ethyl-1-(4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl)-propyl}-2-methyl-phenol

Participants

Reaction Steps

A 1 M solution of LiAlH4 in tetrahydrofuran (5.28 mL, 5.28 mmol) was added to a solution of 4-{1-ethyl-1-(4-(3-ethyl-3-hydroxy-1-pentynyl)-3-methyl-phenyl)-propyl}-2-methyl-phenol (Example 1-(4); 800 mg, 2.11 mmol) in tetrahydrofuran (8 mL) at room temperature. The mixture was heated under reflux for 18 hours and cooled, and then water was added. The mixture was filtered, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column (hexane/ethyl acetate=7/1) to give the title compound (500 mg, 62%).

Provenance & Evidence