Sodium hydride → HCID 57908784, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (720 mg, 18.0 mmol) 60% in mineral oil was suspended in dry DMF (10 mL) and a solution of dimethyl acetamidomalonate (3.00 g, 15 mmol) in dry DMF (10 mL) was added. The solution was stirred at 0° C. for 3 h until the anion had formed. A solution of 4 (2.12 g, 6.0 mmol) in dry DMF (10 mL) was added and the solution warmed to room temperature and stirred overnight. The mixture was poured into distilled water (50 mL), acidified to pH 3 with 1M hydrochloric acid in an ice-bath and extracted into ethyl acetate (3×50 mL). The organic phases were washed with brine (2×30 mL) and dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (Silica gel, 40% EtOAc in hexanes) to give 0.420 g compound 5 (15%). 1H NMR (300 MHz, CDCl3) δ 0.85 (t, 3H, J=6.22 Hz), 1.24 (m, 10H), 1.58 (p, 2H, J=6.95 Hz), 1.97 (s, 3H), 2.45-2.60 (m, 4H), 2.83-3.21 (m, 4H), 3.88 (dd, 1H, J=14.00 Hz, 3.68 Hz), 4.05 (s, 6H), 6.86 (s, 1H), 7.03 (s, 1H), 7.07 (d, 1H, J=8.69 Hz), 7.84 (d, 1H, J=8.36 Hz).

Provenance & Evidence