Reacción #322045

Ecuación de reacción

HCl

potassium t-butoxide

dibenzyl phosphite

lauryl bromide

→

dibenzyl phosphate

Dibenzyl dodecanephosphonate

Disolventes

DMF

DMF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for an additional 1 h
2. 2
   OtroAfter completion of the reaction
3. 3
   Extracciónextracted with ethyl acetate (200 mL)
4. 4
   Otrothe organic phase was dried
5. 5
   Concentraciónconcentrated
6. 6
   Otropurified by flash chromatography

Procedimiento

To a solution of potassium t-butoxide (6.16 g, 55 mmol), in dry DMF (50 mL), under an argon atmosphere was added dropwise via syringe a solution of dibenzyl phosphite (13.1 g, 50 mmol) in dry DMF (5 mL), and the reaction mixture was stirred at room temperature for 20 min. Then a solution of lauryl bromide (18.6 g, 75 mmol) in dry THF (15 mL), was added dropwise under argon atmosphere, and the mixture was stirred at room temperature for an additional 1 h. After completion of the reaction, the mixture was neutralized with dilute HCl (40 mL) and extracted with ethyl acetate (200 mL), the organic phase was dried, concentrated, and purified by flash chromatography to afford the pure dibenzyl phosphate 14 as a colorless oil (Rf 0.46, silica, ethyl acetate and hexane, 1:2, 10.5 g, 50%).

Fuente