Furan → Phosphonic acid, 2-furanyl-, diethyl ester

HRID 1181192Notes

Reaction equation

HRID 1181192 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Li]CCCC.[P:11](Cl)([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12]>C(OCC)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[P:11]([O:16][CH2:17][CH3:18])(=[O:12])[O:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8029FuranHCID 13139Diethyl chlorophosphateHCID 178418339Butyllithium

Product 1

HCID 12485182Phosphonic acid, 2-furanyl-, diethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of furan (1 mmol) in diethyl ether was, treated with TMEDA (N,N,N′N′-tetramethylethylenediamine) (1 mmol) and nBuLi (2 mmol) at −78° C. The solution was stirred for 0.5 h. at −78° C. and diethyl chlorophosphate was added and stirred for another 1 h. Extraction and distillation produced diethyl 2-furanphosphonate as a clear oil.

Workup

  1. stirringstirred for another 1 h
  2. extractionExtraction and distillation

Sources & evidence

ORD record
ord-93f81d8bb730453ca6b54543803d08b9
Source dataset
uspto-grants-2007_10
Patent number
US07285543B2

Reaction notes

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