Methyl formate → Diethyl (5-formylfuran-2-yl)phosphonate

HRID 354020

Reaction equation

HRID 354020 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[P:6]([O:11][CH2:12][CH3:13])(=[O:10])[O:7][CH2:8][CH3:9].[Li+].CC([N-]C(C)C)C.[CH:22](OC)=[O:23]>C1COCC1>[CH2:12]([O:11][P:6]([C:2]1[O:1][C:5]([CH:22]=[O:23])=[CH:4][CH:3]=1)([O:7][CH2:8][CH3:9])=[O:10])[CH3:13]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 2724682Lithium diisopropylamideHCID 12485182Phosphonic acid, 2-furanyl-, diethyl ester

Product 1

HCID 46784019Diethyl (5-formylfuran-2-yl)phosphonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of diethyl 2-furanphosphonate (1 mmole) in THF was treated with LDA (1.12 mmole, lithium N,N-diisopropylamide) at −78° C. for 20 min. Methyl formate (1.5 mmole) was added and the reaction was stirred for 1 h. Extraction and chromatography gave compound 1 as a clear yellow oil. Preferably this aldehyde can be prepared from 2-furaldehyde as described below.

Workup

  1. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-e7ea51fa112449b7a3cf215aa3eb9143
Source dataset
uspto-grants-2004_06
Patent number
US06756360B1

Linked notes

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