Hydrochloric Acid → HCID 58378341, compound

Participants

Reaction Steps

To a solution of isoamyl alcohol (1.0 g, 13.5 mmol) in CH2Cl2 (30 ml) is added 4-nitrophenyl carbonochloridate (3.2 g, 16.2 mmol), 2,4,6-collidine (2.14 ml, 16.2 mmol) and a catalytic amount of DMAP. After stirring for 2 h, 1N HCl is added and the aqueous layer is extracted with CH2Cl2, and the combined organic layers washed with 1N HCl, brine, and dried over Na2SO4. Evaporation of solvent and purification by flash chromatography (120 g SiO2, EtOAc/hexanes gradient) yields sec-butyl 4-nitrophenyl carbonate F5a as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ=8.27 (d, J=9.2 Hz, 2H), 7.38 (d, J=9.2 Hz, 2H), 4.85 (sextet, J=6.4 Hz, 1H), 1.82-1.62 (m, 2H), 1.37 (d, J=6.4 Hz, 3H), 1.00 (t, J=7.2 Hz, 3H); MS calcd. for [M+Na]+C11H13NaNO5: 262.1. found: 262.2.

Provenance & Evidence