Ethyl formate → HCID 86759857, compound

Participants

Reaction Steps

A mixture of ethyl (2RS,3RS)-3-(4-nitrophenyl-2-oxirane carboxylate [prepared by the method of Moyna, G., Williams, H. J., Scott, A. I., Synth. Commun, (1996) 26, 2235-9] (2.5 g, 10.5 mmol) sodium azide (3.4 g, 52.5 mmol), ethyl formate (10 ml) in EtOH/water (8:1, 50 ml) was heated at 50° overnight. The mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4) and evaporated in vacuo. Column chromatography (SiO2; MeOH/DCM, 1:99) gave the title compound as a yellow oil (2.34 g) (less polar regioisomer). δH (CDCl3) 8.24 (2H, d, J 8.8 Hz, ArH), 7.55 (2H, d, J 8.9 Hz, ArH), 5.02 (1H, d, J 3.7 Hz, CHN3), 4.57 (1H, dd, J 5.3, 3.7 Hz, CHOH), 4.25-4.14 (2H, m, CO2CH2), 3.15 (1H, d, J 5.5 Hz, OH), 1.21 (3H, t, J 7.2 Hz, CO2CH2CH3). m/z (ES+, 70V) 253 (M+−N2).

Provenance & Evidence