Sodium hydride → Diethyl 3-methoxyphenylmethoxymethylphosphonate

HRID 2222115Notes

Reaction equation

HRID 2222115 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].[H-].[Na+].O([CH2:21][P:22]([O:27][CH2:28][CH3:29])([O:24][CH2:25][CH3:26])=[O:23])S(C(F)(F)F)(=O)=O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][O:7][CH2:21][P:22](=[O:23])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 814373-Methoxybenzyl alcoholHCID 11833487(Diethoxyphosphoryl)methyl trifluoromethanesulfonate

Product 1

HCID 57457789Diethyl 3-methoxyphenylmethoxymethylphosphonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 3-methoxybenzyl alcohol (1 mmol) and sodium hydride (1.5 mmol) in 5 mL DMF was stirred at rt for 1 h and then added via cannula to a solution of diethylphosphonomethyl triflate (1 mmol) in 5 mL of DMF and the resulting mixture stirred at rt for 16 h. Extraction and chromatography provided diethyl 3-methoxyphenylmethoxymethylphosphonate as an oil.

Workup

  1. stirringthe resulting mixture stirred at rt for 16 h
  2. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-29d8e591a7e847ed847aece255246ad8
Source dataset
uspto-grants-2008_05
Patent number
US07371739B2

Reaction notes

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