Methyl formate → 5-Diethylphosphono-2-thiophenecarboxaldehyde

HRID 2185132Notes

Reaction equation

HRID 2185132 reaction equation
[S: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]>O1CCCC1>[CH2:12]([O:11][P:6]([C:2]1[S: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 42543912-Diethylphosphonothiophene

Product 1

HCID 222749525-Diethylphosphono-2-thiophenecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution 1.0 mmol of diethyl 2-thiophenephosphonate in tetrahydrofuran was treated with 1.12 mmol LDA at −78° C. for 20 min. 1.5 mmol methyl formate was added and the reaction was stirred for 1 hr. Extraction and chromotagraphy gave 5-diethylphosphono-2-thiophenecarboxaldehyde as a clear yellow oil.

Workup

  1. extractionExtraction and chromotagraphy

Sources & evidence

ORD record
ord-54a92a831e5347908ab4a5296adbe6f5
Source dataset
uspto-grants-2002_06
Patent number
US06399782B1

Reaction notes

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