Sodium hydride → HCID 68312962, compound

Participants

Reaction Steps

To an ice-cooled solution of 2-cyclopropylmethylmalonic acid diethyl ester (1.3 g, 6.067 mmol) in THF (45 mL) was added, portionwise, sodium hydride (0.485 g, 60% in oil, 12.13 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 (1.19 g, 6.67 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 2-8% EtOAc in cyclohexane) affording the title compound as a colourless oil (1.55 g, 87%). 1H NMR (CDCl3, 300 MHz): δ 4.33-4.22 (4H, m), 2.24 (2H, d, J=6.6 Hz) 1.30 (6H, d, J=7.1 Hz) 1.01-0.88 (1H, m), 0.54-0.48 (2H, m), 0.17-0.12 (2H, m).

Provenance & Evidence