Ammonium formate → HCID 11157748, compound

Participants

Reaction Steps

Add dry Pd/C (0.110 g, 0.104 mmol) to 6-benzyloxy-2-(4-methoxy-phenyl)-1-{4-[4-(4,4,5,5,5-pentafluoro-pentylsulfanyl)-butoxy]phenoxy}-naphtalene (0.590 g, 0.847 mmol). Add EtOH (25 mL), followed by ammonium formate (0.382 g, 6.058 mmol). Heat to reflux and stirred for 1.5 hours. Cool to room temperature and add additional Pd/C (0.610 g, 0.547 mmol), and ammonium formate (0.385 g, 6.105 mmol). Heat to reflux and stirred for 3 hours. Add celite (10 g) and filter washing with CH2Cl2 and CH3OH. Concentrate the solution in vacuo. Dissolve the resulting residue in CH2Cl2 (20 mL) and wash the solution with H2O (2×15 mL). Separate the layers and dry the organic (Na2SO4), filter and concentrate in vacuo. Purify by radial chromatography (eluting with 30% EtOAc in hexanes) to afford 0.318 g (62%) of the desired 6-(4-methoxy-phenyl)-5-{4-[4-(4,4,5,5,5-pentafluoro-pentylsulfanyl)-butoxy]-phenoxy}-naphthalen-2-ol as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.83 (t, J=9.3 Hz, 1H), 7.58 (d, J=8.3 Hz, 1H), 7.47 (m, 3H), 7.16 (d, J=2.4 Hz, 1H), 7.0 (m, 1H), 6.83 (dd, J=2.0, 6.8 Hz, 2H), 6.58 (m, 4H), 3.81 (t, J=5.9 Hz, 2H), 3.76 (s, 3H), 2.65-2.75 (m, 2H), 2.54 (m, 2H), 2.06-2.29 (m, 3H), 1.68-1.93 (m, 5H).

Provenance & Evidence