Dimethylformamide → HCID 57162619, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion in oil) (1.32 g, 33.0 mmol) was added to a solution of 3-nitro-benzaldehyde (4.53 g, 30.0 mmol) and tert-butyl-bromoacetate (4.87 ml, 33.0 mmol) in DMF (100 ml). The resulting suspension was heated at 65° C. for 2 h, cooled, then quenched with water (10 ml). The mixture was diluted with ethyl acetate (100 ml), the organic phase was washed with water (150 ml), brine (2×150 ml), dried (MgSO4) and the solvent was evaporated. The residue was dissolved in dioxan (50 ml) and hydrogenated over palladium on charcoal (10%, 1.00 g) for 24 h. The catalyst was removed by filtration and the solvent was evaporated. The crude product was purified by flash column chromatography (silica, hexane/ethyl acetate 1:1) to afford colourless oil (2.95 g, 41%). 1H NMR (300 MHz, CDCl3) 7.07 (1H, m), 6.60 (3H, m), 4.30 (1H, dd), 3.61 (2H, br s), 3.00 (1H, dd), 2.85 (2H, m), 1.46 (9H, s).

Provenance & Evidence