m-Chloroperbenzoic acid → HCID 18330057, compound

Participants

Reaction Steps

A solution of 7-nitro-3,4-dihydronaphthalene (9.18 g; 0.052 mol) (from Preparation 2) in CH2Cl2 (600 ml) was cooled to 0° C. and treated with m-CPBA, 57-85%, (13.86 g, approx. 0.056 mol, approx. 1.1 equiv). The reaction mixture was allowed to stir for 48 h, slowly warming to room temperature. The mixture was treated with aqueous NaHCO3 (300 ml) and the organic layer was separated. The organic layer was extracted with additional aqueous NaHCO3, washed with aqueous NaCl, dried (Na2SO4), filtered and concentrated under reduced pressure to give 1,2-epoxy-7-nitro-3,4-dihydronaphthalene (9.94, 100%) as a white solid which was used in the next step without further purification. Rf (silica gel): 0.56(70% hexane: 30% EtOAc); 1H NMR (300 MHZ, CDCl3) 8.24 (s, 1H), 8.08 (dd, J=1.8 and 8.1 H 1H), 7.23 (d, J=8.1 Hz, 1H), 3.92 (d, J=4.2 Hz, 1H), 3.77 (s, 1H), 2.87-2.62 (m, 2H), 2.47 (dd, J=6.6 and 14.4 Hz, 1H), 1.78 (dt, J=5.7 and 14.1 Hz, 1H), 13C NMR (75 MHZ, CDCl3) 146.5, 144.7, 134.5, 129.4, 124.4, 123.4, 54.7, 51.8, 24.5, 21.0.

Provenance & Evidence