Sodium hydride → ethyl 3-amino-5-tert-butylfuran-2-carboxylate

Participants

Reaction Steps

To a slurry of sodium hydride (62 mg, 2.6 mmol, 1.1 equiv) in anh. THF (50 mL) was added (Z)-4,4-dimethyl-3-(ethoxycarbonylmethoxy)pentenenitrile (0.50 g, 2.4 mmol). The reaction mixture was stirred for 3 h, treated with a saturated aq. NH4Cl solution (2 mL), and concentrated under reduced pressure. The residue was purified by flash chromatography (50 g SiO2, 10% EtOAc/hex) to afford ethyl 3-amino-5-tert-butylfuran-2-carboxylate (0.44 g, 88%) as a white solid: mp 44-45° C.; TLC (10% EtOAc/hex) Rf0.19; 1H NMR (CDCl3) δ1.26 (s, 9H), 1.36 (t, J=7.0 Hz, 3H), 4.32 (q, J=7.0 Hz, 2H), 4.51 (br s, 2H), 5.75 (s, 1H); FAB-LRMS m/z (rel abundance) 212 (M+H, 100%). Anal. Calcd for C11H17NO3: C, 62.54; H, 8.11; N, 6.63. Found: C, 62.48; H, 8.06; N, 6.61.

Provenance & Evidence