trans-2-(5-Propylsulfonyl-4-benzyloxy-3-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran → trans-2-(5-propylsulfonyl-4-Hydroxy-3-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran

Participants

Reaction Steps

A solution of trans-2-(3-n-propylsulfonyl-4-benzyloxy-5-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (5.0 g) in ethyl acetate (100 mL) was hydrogenated over 10% palladium-over-charcoal (250 mg) for 1 h. The catalyst was filtered off and the filtrate was concentrated to a crystalline mass. Recrystallization from ethyl ether gave pure product: mp 168°-169° C.; NMR (CDCl3) δ 1.0 (t, CH2CH2CH3), 1.7 (m, CH2CH2CH3), 2.0 & 2.49 (2 m, H-3 & H-4), 3.4 (m, CH2CH2CH3), 3.84, 3.89 & 3.93 (3 s, 4 OCH3), 5.20 (m, H-2 & H-5), 6.62 (s, C5ArH), 7.24 & 7.47 (2 d, J=1.5 Hz, C2ArH).

Provenance & Evidence