3-Biphenyl-4-yl-2,5-dihydro-2,5-dimethoxyfuran → 3-Biphenyl-4-yl-2,5-dimethoxytetrahydrofuran

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Reaction Steps

A mixture of 3-biphenyl-4-yl-2,5-dihydro-2,5-dimethoxyfuran (1.00 g, 3.55 mmol) and 5% Pd/C (300 mg) in EtOH:EtOAc (1:2) was stirred under H2 atmosphere for 1.75 hours. The catalyst was filtered onto Celite. The filtrate was concentrated to provide 0.97 g (97%) of a diastereomeric mixture of 3-biphenyl-4-yl-2,5-dimethoxy-tetrahydro-furan as a colorless oil which was typically used without purification. 1H NMR: δ 7.60-7.53 (m, 4H), 7.45-7.28 (m, 5H), 5.26 (t, 1H, J=5.5 Hz), 5.02 (d, 1H, J=4.4 Hz), 3.54 (s, 3H), 3.36 (s, 3H), 2.63-2.53 (m, 1H), 2.41-2.30 (m, 1H). Anal. calculated for C18H20O3: C, 76.03; H, 7.09. Found: C, 75.74; H, 6.92.

Provenance & Evidence