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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%).

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 (