Triphenylphosphine → HCID 59199400, compound

Participants

Reaction Steps

To a suspension of trifluoro-methanesulfonic acid 5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester (5.0 g, 0.016 mol) and isopropyl 4-imidazolecarboxylate, which can be prepared as described in Example 1 (1.72 g, 0.011 mol) in THF (100 mL) at 0° C. is added triphenylphosphine (4.20 g, 0.016 mol) and dimethyl azodicarboxylate (40% wt. in, toluene, 5.85 g, 0.016 mol). After 1 hour, the mixture is diluted with ethyl acetate and washed with water. The organic phase is dried with Na2SO4, filtered, and concentrated to give a residue, which is purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures) to give 3-(6-trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; 1H NMR (400 MHz, MeOD) δ ppm 1.37 (t, J=6.8 Hz, 6 H), 1.88-1.97 (m, 2 H), 2.27-2.34 (m, 2 H), 2.96 (dd, J=17.4, 6.3 Hz, 1 H), 3.11 (dd, J=17.4, 6.6 Hz, 1 H), 5.22 (t, J=6.8 Hz, 1 H), 6.36 (t, J=6.2 Hz, 1 H), 7.06 (d, J=8.8 Hz, 1 H), 7.19 (dd, J=8.8, 2.5 Hz, 1 H), 7.29 (d, J=2.5 Hz, 1 H), 7.58 (s, 1 H), 7.76 (d, J=1.0 Hz, 1 H).

Provenance & Evidence