Potassium Carbonate → HCID 59363840, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3-Hydroxy-phenyl)-carbamic acid tert-butyl ester (2.4 g, 11.4 mmol) in 5 ml of dry DMF, anhydrous potassium carbonate (7.9 g, 57.416 mmol) was added. The mixture stirred for 5-10 minutes, added ethyl-2-bromo-isobutyrate (4.5 g, 22.9 mmol). The resulting mixture was heated at 70° C. for 12 hours. Upon completion (˜25 h), the solution was diluted with EtOAc (25 ml) and washed with saturated NH4Cl (5 ml). The aqueous layer was then extracted for two additional times with EtOAc (10 ml) and the combined organic fractions were washed with brine (2×5 ml). The solution was then dried over Na2SO4 and concentrated to give brown oil. Purification on silica gel (hexanes/acetone) yielded 1.8 g (49%). 1H-NMR (400 MHz, CDCl3): δ 1H NMR (400 MHz, CDCl3): 1.26 (t, J=7.2 Hz, 3H), 1.50 (s, 9H), 1.59 (s, 6H), 6.43 (s, 1H), 6.47-6.50 (m, 1H), 6.96 (t, J=8.4 Hz, 2H), 7.11 (t, J=8.0, 1H).

Provenance & Evidence