(4-Phenylfuran-3-yl)methanol → 4-Phenyl-3-furaldehyde

Participants

Reaction Conditions

Reaction Steps

Prepare a solution of (4-phenylfuran-3-yl)methanol (2.3 g, 13.2 mmol) in methylene chloride (20 mL). Add N-methylmorpoline N-oxide (2.2 g, 18.5 mmol) and powdered 4 Å molecular sieves. Cool the mixture to 0° C. and add tetra-n-propyl ammonium perruthenate. Warm the mixture to room temperature and stir for an additional 3 hours. Filter the reaction mixture through Celite® and concentrate the filtrate. Perform flash chromatography on silica gel eluting with 10% diethyl ether/hexane to afford 1.36 g of 4-phenyl-3-formylfuran. 1H NMR (CDCl3) δ 10.01 (s, 1H), 8.15 (s, 1H), 7.60 (s, 1H), 7.35-7.54 (m, 5H).

Provenance & Evidence