6-[2-(4-Benzyloxy-phenyl)-ethyl]-6-butyl-4-hydroxy-5,6-dihydro-pyran-2-one → 6-Butyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Participants

Reaction Steps

The title compound was prepared by debenzylation of 1.7 g (4.5 mmol) of 6-[2-(4-benzyloxy-phenyl)-ethyl]-6-butyl-4-hydroxy-5,6-dihydro-pyran-2-one (prepared in the paragraph above) using 0.15 g of 20% Pd on carbon and 75 mL of THF under hydrogen atmosphere as described in General Method 4. 1H NMR (DMSO-d6) δ 0.80 (t, 3 H), 1.2 (m, 4 H), 1.61 (m, 4 H), 1.81 (m, 2 H), 2.38 (d of ABX q, 1 H), 2.49 (d of ABX q, partially obscured by DMSO, 1 H), 4.89 (s, 1 H), 6.6 (d, 2 H), 6.91 (d, 2 H), 9.08 (s, 1 H), 11.25 (s, 1 H).

Provenance & Evidence