Réaction #1552045

Équation de réaction

2-hydroxyvinyl carbamate

THF

triethylamine

diethylchlorophosphonite

THF

→

title compound

2-(diethoxyphosphoryloxy)ethylamine vinyl carbamate

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter completion of the addition
2. 2
   FiltrationA white solid was filtered off
3. 3
   Lavagethe residue was washed with a 5% aqueous solution of sodium hydrogen carbonate (3×10 ml)
4. 4
   SéchageThe organic phase was then dried over sodium sulfate
5. 5
   FiltrationAfter filtering off the siccative, the solvent
6. 6
   Autrewas removed on a rotary evaporator
7. 7
   AutreThe crude product was purified by column chromatography on silica gel (PE:EE=1:5)

Mode opératoire

0.81 ml of triethylamine (5.8 mmol) were precharged in 10 ml of abs. THF, and 0.76 g of 2-hydroxyvinyl carbamate (5.8 mmol) were added. The reaction solution was then cooled to −78° C., and 0.83 ml of diethylchlorophosphonite (5.8 mmol) in 4 ml of THF were added dropwise. After completion of the addition, the reaction mixture was stirred for 12 hours at room temperature. A white solid was filtered off, and the residue was washed with a 5% aqueous solution of sodium hydrogen carbonate (3×10 ml). The organic phase was then dried over sodium sulfate. After filtering off the siccative, the solvent was removed on a rotary evaporator. The crude product was purified by column chromatography on silica gel (PE:EE=1:5). 0.39 g (25% of th.) of the title compound were obtained as a colorless oil.

Source