2-Nitrothiophene-4-carboxaldehyde → HCID 9860933, compound

HRID 1604735Notes

Reaction equation

HRID 1604735 reaction equation
[N+:1]([C:4]1[S:5][CH:6]=[C:7]([CH:9]=[O:10])[CH:8]=1)([O-:3])=[O:2].[P:11]([O-:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]>CO>[N+:1]([C:4]1[S:5][CH:6]=[C:7]([CH:9]([P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[OH:10])[CH:8]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 1447302-Nitrothiophene-4-carboxaldehydeHCID 3780918Diethylphosphite

Product 1

HCID 9860933HCID 9860933, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution containing 2-nitro-4-thiophenecarboxaldehyde (2.61 g, 16.6 mmol), diethyl phosphite (2.14 mL, 16.6 mmol), and methanol (5 mis) was adsorbed onto excess basic alumina. After 16 hours the product was extracted with methylene chloride, concentrated and purified by column chromatography (silica gel). Elution with methylene chloride-methanol 19:1 gave the product (3.55 g) as an oil. 1H NMR (CDC13): d, 5.05 (dd,1H,PCH), 4.15 (m,4H,CH2), 1.33 (dt,6H,CH3). MS (DCl): 296 (MH+). C9H14NO6PS.

Workup

  1. extractionAfter 16 hours the product was extracted with methylene chloride
  2. concentrationconcentrated
  3. custompurified by column chromatography (silica gel)
  4. washElution with methylene chloride-methanol 19:1

Sources & evidence

ORD record
ord-779957d2d513477bbaccf3c0fa5ea775
Source dataset
uspto-grants-1999_11
Patent number
US05994563

Reaction notes

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