2-Thiophenecarboxaldehyde → HCID 178498417, compound

Participants

Reaction Steps

The reaction of hydroxylamine 82 (0.71 g, 2 mmol) with 2-thiophenecarboxaldehyde (64) (0.224 g, 2 mmol) afforded after workup, a light yellow oil. The crude product was purified by flash chromatography with 1:1 ethyl acetate/petroleum ether as the eluant to obtain 0.64 g (1.41 mmol, 71%) of 87 as a light yellow oil. The oil crystallized from ether/pentane to yield yellow crystalline solid: mp 106°-109° C.; IR (CH2Cl2) 3440, 2940, 1695, 1620, 1555, 1470, 1375, 1300, 1215, 1100 cm-1 ; 1H NMR (CDCl3) δ 1.10 (d, J=6.2 Hz, 3H), 1.22 (d, J=6.2 Hz, 3H), 2.27 (s, 6H), 3.61 (s, 3H), 4.94 (septet, J=6.2 Hz, 1H), 5.06 (s, 1H), 6.98 (s, 1H), 7.17-7.77 (m, 7H), 8.44 (s, 1H); 13C NMR (CDCl3) δ 19.87, 22.49, 22.74, 40.59, 51.54, 67.68, 103.30, 104.00, 119.18, 121.52, 127.64, 128,95, 129.76, 130.60, 130.66, 131.78, 133.49, 145.64, 146.13, 147.07, 150.57, 167.62, 168.64. Anal. Calcd for C24H26N2O5S: C, 63.43; H, 5.72. Found: C, 63.26; H, 5.72.

Provenance & Evidence