Trifluoroacetic acid → HCID 22598375, compound

Participants

Reaction Steps

A solution of tridecanal (25.00 g, 126.04 mmol) and trifluoroacetic acid (2.00 g) in anhydrous dichloromethane (200 mL) was added dropwise to a solution of 3-aminothiophene (21.00 g, 211.78 mmol) in anhydrous dichloromethane (200 mL) at −10° C. The reaction mixture was stirred at room temperature for 1.5 h. Trifluoroacetic acid (24.15 g, 211.78 mmol) was added and the reaction mixture was then heated at reflux for 24 h. The solution was cooled and diethyl ether (300 mL) and water (100 mL) were added. The aqueous layer was basified with 0.5 N aqueous sodium hydroxide solution. The organic layer was separated. The aqueous layer was again extracted into diethyl ether (2×100 mL). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography (eluent: dichloromethane) afforded 4-dodecyldithieno[3,2-b:2′3′-e]pyridine (16.74 g, 22%) as a red oil: δH(CDCl3, 300 MHz) 7.76 (2H, d, 3JHH=6 Hz), 7.60 (2H, d, 3JHH=6 Hz), 3.15 (2H, t, 3JHH=7.5 Hz), 1.90 (2H, m), 1.25-1.50 (18H, m), 0.88 (3H, t, 3JHH=7.5 Hz); δC(CDCl3, 75 MHz) 155.8, 140.0, 130.3, 129.4, 125.3, 34.5, 31.9, 29.7, 29.6, 29.5, 29.4, 28.0, 22.7, 14.1.

Provenance & Evidence