Acetic Acid → HCID 14410100, compound

N-butyl lithium in hexane (1.62N, 38.1 ml, 0.0617 mol) was added dropwise under argon atmosphere to a solution of dimethyl methylphosphonate (7.0 ml, 0.0643 mol) in anhydrous THF (100 ml) at -78° C. The reaction mixture was stirred for 30 min. To the mixture was added dropwise methyl 2-methyl-2-phenoxypropionate (5.00 g, 0.0257 mol), and the mixture was stirred for 20 min. at -78° C. and further stirred for 30 min. at room temperature. To the resulting mixture were added 10 ml of water and acetic acid (3.2 ml, 0.0559 mol), and then the mixture was concentrated. The residue was extracted with ethyl acetate (50 ml×4). The combined ethyl acetate layers were washed with 50 ml of water and with 50 ml of brine, dried over anhydrous sodium sulfate, and concentrated. The residue thus obtained was purified by column chromatography (silica gel, ethyl acetate/cyclohexane: 3/1) to give a purified dimethyl 3-methyl-2-oxo-3-phenoxybutylphosphonate (6.5867 g, 0.0257 mol, 100%). The product was assigned the structure by the following data.

1. stirringthe mixture was stirred for 20 min. at -78° C.
2. stirringfurther stirred for 30 min. at room temperature
3. concentrationthe mixture was concentrated
4. extractionThe residue was extracted with ethyl acetate (50 ml×4)
5. washThe combined ethyl acetate layers were washed with 50 ml of water and with 50 ml of brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated
8. customThe residue thus obtained
9. customwas purified by column chromatography (silica gel, ethyl acetate/cyclohexane: 3/1)

ORD record

ord-d7d2fda2d3454a62b1eff7714b49e7b3

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04775692