Hydrochloric Acid → 3-Dodecylthiophene-2-carbaldehyde

HRID 888672Notes

Reaction equation

HRID 888672 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

After magnesium (0.63 g; 25.8 mmol) and anhydrous THF (25 ml) were put into a flask, 2-bromo-3-dodecylthiophene (7.78 g; 23.5 mmol) was slowly added 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 layer was extracted by using ethyl ether, and the obtained organic layer was washed sequentially with NaHCO3, a saturated NaCl aqueous solution, and water. The residual moisture was removed over anhydrous magnesium sulfate. After removing the solvent, the residue was subjected to a column separation process by 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 layer was extracted
  7. washthe obtained organic layer was washed sequentially with NaHCO3
  8. customThe residual moisture was removed over anhydrous magnesium sulfate
  9. customAfter removing the solvent
  10. customthe residue was subjected to a column separation process

Sources & evidence

ORD record
ord-30004d5a8582409caf29ddeb46b4b090
Source dataset
uspto-grants-2012_08
Patent number
US08247803B2

Reaction notes

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