Dimethyl methylphosphonate → HCID 20082137, compound

To a solution of dimethyl methylphosphonate (6.6 ml, 60.5 mmol) in 100 ml of anhydrous THF was added dropwise n-butyl lithium (1.59N, 38.1 ml, 60.5 mmol) at -78° C. under argon atmosphere, and the mixture was stirred for 30 minutes. Then, methyl 3-cyclohexyl-2,2-dimethylpropionate (5.00 g, 25.2 mmol) was added dropwise and the mixture was stirred at -78° C. for 20 minutes and then at room temperature for 2 hours. An aqueous saturated solution of ammonium chloride was added to the reaction mixture. The mixture was extracted with ethyl acetate (50 ml×4) and then the combined ethyl acetate layers were washed with water (50 ml) and brine (50 ml), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography (silica gel, ethyl acetate) to yield a pure product of dimethyl 4-cyclohexyl-3,3-dimethyl-2-oxobutylphosphonate (3.9491 g, 13.6 mmol, 54.0%). This compound was assigned the structure by the following data:

1. stirringthe mixture was stirred at -78° C. for 20 minutes
2. waitat room temperature for 2 hours
3. extractionThe mixture was extracted with ethyl acetate (50 ml×4)
4. washthe combined ethyl acetate layers were washed with water (50 ml) and brine (50 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated
7. customThe residue was purified by column chromatography (silica gel, ethyl acetate)

ORD record

ord-80c8ce5cfa634cb796dcdc0c8a508ce5

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04775692