1,8-Diazabicyclo(5.4.0)undec-7-ene → Bis(2,2,2-trifluoroethyl)(1-triphenylmethylimidazol-4-yl)methylphosphonate

To a solution of bis(2,2,2-trifluoroethyl)phosphite (0.11 ml, 0.6 mmol) in THF (1.5 ml) were added 1,8-diazabicyclo[5,4,0]-7-undecene (DBU) (0.09 ml, 0.6 mmol) and (1-triphenylmethylimidazol-4-yl)methyl chloride (71.8 mg, 0.2 mmol). The reaction mixture was refluxed under argon flow for 22 hours. The solvent was removed under reduced pressure, and water (10 ml) was added to the residue, which was then extracted 3 times with ethyl acetate (10 ml). The resultant organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained white solid was purified through chromatography on silica gel column using ethyl acetate-hexane (3:2) to give bis(2,2,2-trifluoroethyl)(1-triphenylmethylimidazol-4-yl)methylphosphonate (34 mg, 30%) as a white powder. This powder was recrystallized from a mixture of ethyl acetate and hexane to provide a white small needle crystal (m.p. 145-148° C.).

1. temperatureThe reaction mixture was refluxed under argon flow for 22 hours
2. customThe solvent was removed under reduced pressure, and water (10 ml)
3. additionwas added to the residue, which
4. extractionwas then extracted 3 times with ethyl acetate (10 ml)
5. washThe resultant organic layers were washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customthe solvent was removed under reduced pressure
8. customThe obtained white solid was purified through chromatography on silica gel column

ORD-Eintrag

ord-1fe4d43c966245fda669b0ebad9e7ddb

Quelldatensatz

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06951944B2