2-Thiophenecarboxaldehyde → HCID 58270231, compound

Participants

Reaction Steps

A stirred solution of Example 3 (6.86 g, 29 mmol) in tetrahydrofuran (200 ml) was treated with dimethylimidazolium iodide (2.13 g, 9.6 mmol), thiophene-2-carbaldehyde (3.19 ml, 35 mmol) and sodium hydride (1.51 g, 38 mmol). The mixture was first stirred at room temperature for 25 min and then heated, with stirring, to 70° C. for 3 h. The reaction mixture was cooled to room temperature and reduced in vacuo. The residue was partitioned between water and dichloromethane. The organic fraction was separated, dried over sodium sulfate and reduced in vacuo. Trituration with methanol gave the title compound in 72% yield, 95% purity. LC-MS m/z=279.1 [M+H]+; RT=3.77 min; LC-MS method 1. 1H NMR: δH (400 MHz, D6-DMSO) 7.40-7.42 (1H, m), 7.95 (1H, s), 8.31 (1H, d, J=4.5 Hz), 8.61 (1H, d, J 4.5 Hz).

Provenance & Evidence