(2S)-7-(Benzyloxy)-1-(4-fluorophenoxy)heptan-2-OL → (6S)-7-(4-fluorophenoxy)-heptane-1,6-diol

Participants

Reaction Steps

To a solution of (2S)-7-Benzyloxy-1-(4-fluorophenoxy)-heptane-2-ol (5.8 g, 17.5 mmol) in ethanol (30 ml), 10% of Pd/C (100 mg) was added and stirred under H2 atmosphere at normal temperature and pressure for 3 hours. The reaction mixture was filtered through celite, washed with ethanol and concentrated. The residue was purified by silicia gel chromatography using EtOAc-hexane (1:1) to give (6S)-7-(4-fluorophenoxy)-heptane-1,6-diol (3.92 g, 93%); [α]D+12 (c 3.1, CHCl3), 1H-NMR (CDCl3, 200 Hz): δ 1.29-1.69 (m, 8H), 3.65 (t, J=6.8 Hz, 2H), 3.82-4.02 (m, 2H), 6.75-7.0 (m, 4H); HRMS (EI): calcd. for C13H19O3F(M+) 242.131823 found 242.131900.

Provenance & Evidence