2-Iodothiophene → HCID 118222843, compound

Participants

Reaction Steps

To a suspension of hexanes-washed sodium hydride (918 mg, 22.95 mmol) in 10 mL anhydrous tetrahydrofuran at 0° C. was added 3,3,3-trifluoropropanol (3.5 g, 30.60 mmol) dropwise. After the addition was complete, the mixture was stirred at room temperature for 30 minutes. 2-Iodothiophene (3.21 g, 15.30 mmol) and copper(I) iodide (728 mg, 3.82 mmol) were added, the reaction vessel was flushed with argon, sealed and stirred at 100° C. for 48 h. The reaction mixture was allowed to cool to room temperature and poured into 150 mL of 5% aqueous potassium cyanide solution. Organics were extracted with 1:1 ether/hexanes (3×100 mL), dried with magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel (100% hexanes) to give 2-(3,3,3-trifluoropropoxyl)thiophene (1.70 g, 57%).

Provenance & Evidence