Sodium hydride → HCID 86671481, compound

Participants

Reaction Steps

To an ice-cooled solution of 2-isobutylmalonic acid diethyl ester (3.21 g, 14.8 mmol) in THF (50 mL) was added portionwise sodium hydride (1.19 g, 60% in oil, 29.7 mmol). The mixture was stirred in the ice bath for 15 min, and then at RT for 15 min. The suspension was re-cooled in the ice bath and NBS (2.9 g, 16.3 mmol) was added over 5 min. The mixture was stirred in the ice bath for 10 min, and then at RT for 30 min. The reaction mixture was filtered through Celite® and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-6% EtOAc in cyclohexane) affording the title compound as a colourless oil (3.828 g, 88%). 1H NMR (CDCl3, 300 MHz): δ 4.27 & 4.26 (4H, 2 q, J=7.1 Hz), 2.26 (2H, d, J=6.2 Hz) 1.95 (1H, nonet, J=6.5 Hz), 1.29 (6H, t, J=7.1 Hz), 0.94 (6H, d, J=6.7 Hz).

Provenance & Evidence