Hydrochloric Acid → 3-Teradecylthiophene-2-carboxaldehyde

HRID 523437Notes

Reaction equation

HRID 523437 reaction equation
[Mg].C1C[O:5][CH2:4]C1.Br[C:8]1[S:9][CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl>CN(C=O)C>[CH2:13]([C:12]1[CH:11]=[CH:10][S:9][C:8]=1[CH:4]=[O:5])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 5462224Magnesium2×HCID 672935902-Bromo-3-tetradecylthiophene

Product 1

HCID 867176823-Teradecylthiophene-2-carboxaldehydeYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Magnesium turnings (0.528 g, 22 mmol) dissolved and 60 mL of dry THF was placed in a 100 mL round bottom flask. 2-Bromo-3-tetradecylthiophene (7.2 g, 20 mmol) was added dropwise to above solution. The mixture was refluxed until almost all the magnesium turnings disappeared. After the mixture was transferred to a clean flask, dry DMF (4 mL) was added dropwise. The mixture was refluxed overnight and cooled in an ice bath. A 5% HCl solution (20 mL) was added to the reaction mixture. The organic portion was extracted by dichloromethane, washed by a 10% KOH solution (50 mL×3), and dried by MgSO4. After removal of the solvent, the crude product was purified by column chromatography on silica gel (using 5% ethyl acetate in hexane as an eluant) to give 3-teradecylthiophene-2-carboxaldehyde as a colorless oil (yield=50%).

Workup

  1. customAfter the mixture was transferred to a clean flask
  2. temperatureThe mixture was refluxed overnight
  3. temperaturecooled in an ice bath
  4. extractionThe organic portion was extracted by dichloromethane
  5. washwashed by a 10% KOH solution (50 mL×3)
  6. dry with materialdried by MgSO4
  7. customAfter removal of the solvent
  8. customthe crude product was purified by column chromatography on silica gel (

Sources & evidence

ORD record
ord-4ba8929bc9914d9998dfdc52626bfb13
Source dataset
uspto-grants-2016_05
Patent number
US09337358B2

Reaction notes

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