Triacetoxyperiodinane → HCID 18962496, compound

Participants

Reaction Steps

5-hydroxymethyl-2-n-propyl-1-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-4-vinylimidazole (470 mg, 0.73 mmol, 1 eq), Dess-Martin periodinane (J. Org. Chem. (1983) 48, 4155) (341 mg, 0.80 mmol, 1.1 eq) and methylene chloride (10mL) were mixed and stirred under nitrogen overnight. The solvent was removed in vacuo and the residue flash chromatographed in 3:2 hexane ethyl acetate over silica gel to yield 310 mg (66%) of a white glass. NMR (DMSO-d6) δ 9.91 (s,1H); 7.80 (d,1H,J=7Hz); 7.61 (t,1H, J=7Hz); 7.54 (t,1H,J=7Hz); 7.48-7.22(m,10H); 7.20 (d,1H,J=9Hz); 7.06 (d,2H,J=9Hz); 7.00-6.75 (m,8H); 6.15 (d of d,1H,J=17,3 Hz); 5.52 (s,2H); 5.47 (d of d,1H,J=12,3 Hz); 2.49 (t,2H,J=7Hz); 1.57 (t of q,2H,J=7,7Hz); 0.79 (t,3H,J=7Hz). IR (neat) 1658 cm-1. Anal. calcd. for C42H36N6O.(H2O)0.5 : C, 77.63; H, 5.74; N, 12.93. Found: C, 77.53; H, 5.73; N, 12.64. ##STR81##

Provenance & Evidence