Potassium Hydroxide → HCID 68596887, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottomed flask was added EtOH (10 mL) and potassium hydroxide (507 mg, 9.05 mmol). The mixture was stirred until homogeneous before adding commercially available 4-hydroxy-3-methyl benzaldehyde (247 mg, 1.81 mmol) and tert-butyl 4-((4-acetyl-3-methylphenoxy)methyl)piperidine-1-carboxylate (630 mg, 1.81 mmol). The reaction was heated to 80° C. for 5 h, cooled to rt, and concentrated via rotary evaporation. The product was dry-loaded onto a silica gel column and purified through flash chromatography (1:1 EtOAc:Hexanes) to afford (E)-tert-butyl 4-((4-(3-(4-hydroxy-3-methylphenyl)acryloyl)-3-methylphenoxy)methyl)piperidine-1-carboxylate (400 mg, 47% yield).

Provenance & Evidence