Hydrochloric Acid → 3-Dodecylthiophene-2-carbaldehyde

HRID 1874017Notes

Reaction equation

HRID 1874017 reaction equation
[Mg].Br[C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].CN([CH:23]=[O:24])C.Cl>C1COCC1>[CH2:8]([C:7]1[CH:6]=[CH:5][S:4][C:3]=1[CH:23]=[O:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 5462224Magnesium2×HCID 104268162-Bromo-3-Dodecylthiophene

Product 1

HCID 201494313-Dodecylthiophene-2-carbaldehydeYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Magnesium (0.63 g; 25.8 mmol) and anhydrous THF (25 ml) were put into a flask, and 2-bromo-3-dodecylthiophene (7.78 g; 23.5 mmol) was added dropwise thereto. After starting Grignard reaction, the solution was refluxed until magnesium was almost removed. The purified DMF (3.65 g; ˜4 ml; 50 mmol) was slowly added dropwise to the reaction solution. The reaction solution was refluxed for one day, and cooled to 0° C., and 5% HCl (100 ml) was added thereto to terminate the reaction. An organic material layer was extracted from ethyl ether, and the obtained organic material layer was washed sequentially with NaHCO3, a saturated NaCl solution, and water. The residual moisture was removed over anhydrous magnesium sulfate. After removing the solvent, the residue was column separated using silica gel (ethyl acetate/hexane=1/9) to obtain 3-dodecylthiophene-2-carboaldehyde (3.6 g; 55%).

Workup

  1. customGrignard reaction
  2. customwas almost removed
  3. temperatureThe reaction solution was refluxed for one day
  4. customto terminate
  5. customthe reaction
  6. extractionAn organic material layer was extracted from ethyl ether
  7. washthe obtained organic material layer was washed sequentially with NaHCO3
  8. customThe residual moisture was removed over anhydrous magnesium sulfate
  9. customAfter removing the solvent
  10. customseparated

Sources & evidence

ORD record
ord-9e3c81b95d844207a710c98c676c7083
Source dataset
uspto-grants-2012_11
Patent number
US08304555B2

Reaction notes

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