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

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%).

1. temperaturecooling, to the suspension
2. stirringthe mixture was stirred at room temperature for 2 hours
3. extractionthe reaction mixture was extracted with ethyl acetate
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe obtained residue was purified through silica gel column chromatography
7. customfurther evaporated under reduced pressure

ORD record

ord-4e7654e7b1a04c2ca8c8cdd5df940224

Source dataset

uspto-grants-1989_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04810805