Dichloromethane → (4-Phenylfuran-3-yl)methanol

Participants

Reaction Steps

Prepare a solution of 4-phenylfuran-3-carboxylic acid ethyl ester (3.9 g, 18.1 mmol) in toluene (20 mL) under nitrogen at −78° C. Add a 1.0 M solution of Diisobutyl aluminium hydride in methylene chloride (35 mL, 35.0 mmol). Stir the reaction mixture for 1 hour, quench with water, and pour into 10% Rochelle's salt (200 mL). Extract the aqueous phase with ethyl acetate (2×200 mL). Wash the organic phase with brine (100 mL), dry (Na2SO4), filter, and concentrate. Flash chromatography on silica gel eluting with 4:1 Hex/ethyl acetate to afford 2.3 g of (4-phenylfuran-3-yl)methanol. 1H NMR (CDCl3) δ 7.51-7.58 (m, 4H), 7.30-7.45 (m, 3H), 4.67 (d, J=5 Hz, 2H).

Provenance & Evidence