Dimethylformamide → (Chloro(phenylmethoxy)phosphoryl)oxymethylbenzene

HRID 30990

Reaktionsgleichung

Reaktionsgleichung von HRID 30990
[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]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 4193600Dibenzylphosphate

Produkt 1

HCID 4641201(Chloro(phenylmethoxy)phosphoryl)oxymethylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-37b1cc5b621449d489a8afc96a527baa
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425553B2

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