Dimethylformamide → (Chloro(phenylmethoxy)phosphoryl)oxymethylbenzene

HRID 2233055Notes

Reaction equation

HRID 2233055 reaction equation
[P:1]([O-])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(Cl)(=O)C([Cl:23])=O.CN(C=O)C>C(Cl)Cl>[P:1]([Cl:23])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 4193600Dibenzylphosphate

Product 1

HCID 4641201(Chloro(phenylmethoxy)phosphoryl)oxymethylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-f4aac0e852d44833a720a26cd646b953
Source dataset
uspto-grants-2010_05
Patent number
US07709477B2

Reaction notes

Loading…