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

HRID 229435

Reaction equation

HRID 229435 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 EtherSolvent2×

Procedure

A solution of furan (1 mmole) in 1 mL diethyl ether was treated with N,N,N′N′-tetramethylethylenediamine (TMEDA) (1 mmole) and nBuLi (1.1 mmole) at −78° C. for 0.5 h. The resulting solution was cannulated into a solution of diethyl chlorophosphate (1.33 mmole) in I mL of diethyl ether at −60° C. and the reaction mixture allowed to rise to rt and stirred for another 16 h. Extraction and distillation at 75° C./0.2 mm produced diethyl 2-furanphosphonate as a clear oil.

Workup

  1. customto rise to rt
  2. extractionExtraction and distillation at 75° C./0.2 mm

Sources & evidence

ORD record
ord-683650f25b8e4335884de80fd5c94842
Source dataset
uspto-grants-2009_07
Patent number
US07563774B2

Linked notes

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