Réaction #322045

Équation de réaction

HCl

potassium t-butoxide

dibenzyl phosphite

lauryl bromide

→

dibenzyl phosphate

Dibenzyl dodecanephosphonate

Solvants

DMF

DMF

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for an additional 1 h
2. 2
   AutreAfter completion of the reaction
3. 3
   Extractionextracted with ethyl acetate (200 mL)
4. 4
   Autrethe organic phase was dried
5. 5
   Concentrationconcentrated
6. 6
   Autrepurified by flash chromatography

Mode opératoire

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%).

Source