HCID 67885369, compound → HCID 86747308, compound

Participants

Reaction Steps

5-Hydroxymethyl-4-[cis-(naphth-1-yl)ethenyl]-2-n-propyl-1-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]imidazole (7.86 g, 10.2 mmol, 1 eq), manganese dioxide (4.44 g, 51.1 mmol, 5 eq), and methylene chloride (25 mL) were mixed and refluxed under N2 overnight. The manganese dioxide was filtered through Celite™ and the cake washed with methylene chloride. The filtrate was evaporated, and the residue flash chromatographed in 75:25 pentane/ethyl acetate to 1:1 pentane/ethyl acetate to yield 3.78 g of an orange lass. NMR (CDCl3) δ 9.37 (s, 1H); 8.04 (m, 1H); 7.92 (d, 1H, J=8 Hz); 7.80 (m, 1H); 7.72 (m, 1H); 7.60-7.10 (m, 16H); 7.10-6.70 (m, 10H); 6.53 (d, 2H, J=8 Hz); 5.30 (s, 2H); 2.38 (t, 2H, J=7 Hz); 1.56 (t of q, 2H, J=7,7 Hz); 0.77 (t, 3H, J=7 Hz). Anal. calcd. for C52H42N6O.(H2O)0.7 : C, 80.12; H, 5.61; N, 10.78. Found: C, 80.24; H, 5.91; N, 10.46. ##STR222##

Provenance & Evidence