Tetrahydrofuran → HCID 18798682, compound

Participants

Reaction Steps

Hydrogenation of 5.20 g (42.6 mmol) of 1,5-bis-(3-benzyloxy-phenyl)-penta-1,4-dien-3-one prepared in Example E was effected as described in General Method 3 using 0.5 g 5% Pd over BaSO4 and 150 mL of THF under hydrogen atmosphere. The product contained both ketone and alcohol, so the mixture was dissolved in acetone (approximately 200 mL) and treated with 5 mL of 8.0N Jones reagent. The mixture was stirred for 2 hours at room temperature, treated with isopropanol, and filtered through Celite. The filtrate was concentrated, and the residue was triturated with 1:1 hexane:EtOAc to give the title compound. 1H NMR (CDCl3) δ 2.69 (m, 4 H), 2.85 (m, 4 H), 5.03 (s, 4 H), 6.58-6.81 (m, 6 H), 7.18 (m, 2 H), 7.28-7.41 (m, 10 H).

Provenance & Evidence