2,5-Dimethylthiophene → 2,5-Dimethylthiophene-3-carbaldehyde

HRID 1045044

Reaction equation

HRID 1045044 reaction equation
O=P(Cl)(Cl)Cl.[CH3:6][C:7]1[S:8][C:9]([CH3:12])=[CH:10][CH:11]=1.[C:13]([O-])(=[O:15])C.[Na+]>CN(C=O)C>[CH3:6][C:7]1[S:8][C:9]([CH3:12])=[CH:10][C:11]=1[CH:13]=[O:15]

Participants

5

Reactant 3

HCID 125142,5-DimethylthiopheneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

Product 1

HCID 27627592,5-Dimethylthiophene-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To DMF (100 mL) stirred in an ice bath was added POCl3 (25 mL) drop wise followed by the addition of 2,5-dimethyl-thiophene (5 mL). The solution was warmed to room temperature and then was heated at 80° C. overnight. The reaction was cooled to room temperature and was slowly added to ice. Sodium acetate was added to bring the pH to between 5 and 6. The aqueous portion was extracted with ethyl acetate, and the organic portion was dried over sodium sulfate, concentrated under reduced pressure and purified on a silica gel column (eluent: 10:1:hexanes:EtOAc→4:1:hexanes:EtOAc to yield 2,5-dimethyl-thiophene-3-carboxaldehyde (1.5 g).

Workup

  1. temperaturewas heated at 80° C. overnight
  2. temperatureThe reaction was cooled to room temperature
  3. additionwas slowly added to ice
  4. extractionThe aqueous portion was extracted with ethyl acetate
  5. dry with materialthe organic portion was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified on a silica gel column (eluent

Sources & evidence

ORD record
ord-442415df1ea74f20aaaf2ca30bc9512b
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Linked notes

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