Methyl formate → Diethyl (5-formylfuran-2-yl)phosphonate
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
Product 1
Reagents, catalysts & solvents 1
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
- extractionExtraction and chromatography
Sources & evidence
- ORD record
- ord-e7ea51fa112449b7a3cf215aa3eb9143
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06756360B1
Reaction notes
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