P,P,P′,P′-Tetraethyl P,P′-ethylidenebis[phosphonate] → HCID 13612965, compound

A solution of 13.29 g (40 mmol) of tetraethyl ethane-1,1-diphosphonate in 120 ml of dry tetrahydrofuran was cooled to -78° C. in an argon atmosphere followed by the addition of 24.24 ml (40 mmol) of a n-butyllithium hexane solution (1.65 mmol/ml) and stirring for 30 minutes. After adding a solution of 7.63 g (40 mmol) of 4-methylthiobenzenesulfenyl chloride in 50 ml of dry tetrahydrofuran to this mixture, the reaction mixture was allowed to warm up to room temperature followed by stirring for 3 hours. After pouring the resulting mixture into icewater, the mixture was extracted with ethyl acetate (3×150 ml). The solvent was distilled off under reduced pressure after the combined organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. A mixture of tetraethyl 1-methylthiophenyl)thio]ethane-1,1-diphosphonate and tetraethyl 1-chloroethane-1,1-diphosphonate was obtained as the residue. This mixture was then carefully purified with column chromatography (developing solvent: ethanol: ethyl acetate=5:95) to obtain 7.12 g of the target compound in the form of a yellow oily substance.

1. stirringby stirring for 3 hours
2. additionAfter pouring the resulting mixture into icewater
3. extractionthe mixture was extracted with ethyl acetate (3×150 ml)
4. distillationThe solvent was distilled off under reduced pressure after the combined organic layer
5. washwas washed with water and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. additionA mixture of tetraethyl 1-methylthiophenyl)thio]ethane-1,1-diphosphonate

ORD record

ord-be1d75ef418047f791d67711a119755c

Source dataset

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05527940