Sodium hydride → Dimethyl (1-chloro-2-oxoheptyl)phosphonate

Participants

Reaction Steps

Under argon gas atmosphere, 60% sodium hydride (1.8 g, 45.0 mmol) was suspended in anhydrous DME (10 ml) and under ice-cooling, to the suspension was added dimethyl(2-oxoheptyl)phosphonate (5.0 g, 22.5 mmol) dissolved in anhydrous DME (40 ml) and the mixture was stirred at the same conditions for 30 minutes. To the mixture was added N-chlorosuccinimide (3.0 g, 22.5 mmol) and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was then added a saturated aqueous ammonium chloride solution and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified through silica gel column chromatography and further evaporated under reduced pressure to obtain dimethyl(1-chloro-2-oxoheptyl)phosphonate (4.4 g, 76%).

Provenance & Evidence