Tetrahydrofuran → 1,5-Bis (4-benzyloxy-phenyl)-pentan-3-one

Participants

Reaction Steps

Hydrogenation of 24.4 g (54.7 mmol) of 1,5-bis-(4-benzyloxy-phenyl)-penta-1,4-dien-3-one prepared in Example A was effected as described in General Method 3 using 1.0 g 5% Pd over BaSO4 and 1000 mL of THF under hydrogen atmosphere. The product contained both ketone and alcohol. Therefore, the mixture was dissolved in acetone (approximately 500 mL), treated with 10 mL of 8.0N Jones reagent, and stirred overnight at room temperature. Isopropanol was added, and the mixture was filtered through Celite. The filtrate was concentrated to afford the title ketone. 1H NMR (CDCl3) δ 2.67 (m, 4 H), 2.82 (m, 4 H), 5.03 (s, 4 H), 6.88 (d, 4 H), 7.05 (d, 4 H), 7.30-7.43 (m, 10 H).

Provenance & Evidence