Diethyl Malonate → HCID 118101242, compound

Participants

Reaction Steps

To sodium hydride (60% dispersion) (1.885 g, 47.1 mmol), was added DMSO (20 mL). The mixture was stirred for 5 min, then diethyl malonate (7.15 mL, 47.1 mmol) was added. The reaction mixture was stirred at rt for 15 min to give a clear colorless solution. To this mixture was added a solution of benzyl 2-fluoro-5-nitrobenzyl(methyl)carbamate (3 g, 9.43 mmol) in DMSO (1 mL) dropwise. The orange reaction mixture was stirred at rt for 1 h, then at 65° C. for 3 h. The reaction mixture was cooled to rt, quenched with sat. NH4Cl. The mixture was diluted with EtOAc. The organic phase was washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (loaded in chloroform onto a 120 g column and eluted with a gradient from 0 to 30% ethyl acetate/hexanes) to give 10A (3.88 g, 8.46 mmol, 90% yield). MS (ESI) m/z: 458.9 (M+H)+.

Provenance & Evidence