Reaction #1552046

Reaction equation

N-butyllithium

diethyl chlorophosphonate

THF

→

title compound

diethyl vinyl phosphate

Conditions

Workup

1. 1
   Otherat 0° C
2. 2
   workup.STIRRINGstirred for 1 h at 0° C.
3. 3
   workup.WAITfor 16 hours at room temperature
4. 4
   FiltrationA white solid was filtered off
5. 5
   Otherthe solvent was removed on a rotary evaporator
6. 6
   OtherThe slightly yellowish crude product was purified by column chromatography on silica gel (PE:EE=4:1)

Procedure

10 ml of N-butyllithium solution (2.1 M solution in hexane) were added dropwise to 50 ml of abs. THF under an argon atmosphere at 0° C. The solution was stirred for 30 minutes at 0° C. and for 15 hours at room temperature, then added to 3.01 ml diethyl chlorophosphonate (20 mmol) at −76° C. and stirred for 1 h at 0° C., then for 16 hours at room temperature. A white solid was filtered off, and the solvent was removed on a rotary evaporator. The slightly yellowish crude product was purified by column chromatography on silica gel (PE:EE=4:1). 2.2 g (60% of th.) of the title compound were obtained as a yellowish liquid.

Source