Reacción #59268

Ecuación de reacción

dibenzyl phosphate

oxalyl chloride

DMF

→

dibenzyl chlorophosphate

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was removed by rotary evaporation
2. 2
   Otrothe residue was dried in vacuo for 2 h

Procedimiento

A solution of dibenzyl phosphate (3.76 g, 13.5 mmol) in CH2Cl2 (10 mL) was treated with oxalyl chloride (1.17, 13.5 mmol) and DMF (0.5 mL). The mixture was stirred at room temperature for 1 h, the solvent was removed by rotary evaporation and the residue was dried in vacuo for 2 h to afford dibenzyl chlorophosphate as a yellowish solid. The residue was suspended in CH2Cl2 (5 mL), cooled to 0° C., treated with a solution of benzylic alcohol M (1.7 g, 6.7 mmol) in CH2Cl2 (5 mL) then DBU (2.02 mL, 13.5 mmol, added dropwise). The mixture was stirred at room temperature for 1 h30, and the solvent was removed by rotary evaporation. The residue was purified by column chromatography over silica gel using a gradient of 0-10% EtOAc/hexane as eluent.

Fuente