Water → HCID 66696641, compound

Participants

Reaction Steps

A mixture of 5-ethylthiophene-2-carbaldehyde (0.670 g, 4.78 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (1.0 g, 4.8 mmol), and K2CO3 (0.859 g, 6.21 mmol) in MeOH (16 mL) was heated at reflux for 2 h, then cooled to room temperature and allowed to stand overnight. The mixture was poured into water and extracted with Et2O, and the combined extracts were concentrated in vacuo. The residue was chromatographed on silica gel (Analogix® SF40-115 column, 15% to 30% EtOAc/hexanes eluant, 18 minutes) to afford 0.94 g (102%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.26 (s, 1H), 7.15 (d, J=3.6, 1H), 6.91 (dt, J=3.7, 1.0 1H), 2.85 (qd, J=7.5, 0.8 2H), 2.29 (s, 3H), 1.26 (t, J=7.5, 3H). MS (DCI+) m/z 194 (M+H).

Provenance & Evidence