Phenol → HCID 66875343, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (Intermediate 20, 2.50 g, 10.03 mmol) in acetonitrile (111 mL, 0.09M) was treated with potassium carbonate (1.38 g, 10.03 mmol) and phenol (944 mg, 10.03 mmol). The resulting reaction mixture was heated at reflux for 3 h and then was allowed to cool to 25° C. The reaction mixture was then partitioned between water (150 mL) and methylene chloride (3×100 mL). The combined organics were dried over sodium sulfate, filtered, rinsed, and concentrated in vacuo. Silica gel column chromatography (ISCO 80 g, 30% ethyl acetate/hexanes) afforded 4-chloro-5-phenoxy-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (2.84 g, 92%) as a clear oil; ES+-HRMS m/e calcd for C15H15N2O3Cl [M+H+] 307.0844, found 307.0843.

Provenance & Evidence