Methyl vinyl ketone → HCID 10776658, compound

Participants

Reaction Conditions

Reaction Steps

In a small vial charged with 4-(trifluoromethyl)benzaldehyde (3.00 mL, 21.98 mmol) in Ethanol (Volume: 9.5 mL) was added triethylamine (6.13 mL, 44.0 mmol), but-3-en-2-one (2 mL, 21.98 mmol), and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium bromide (1.109 g, 4.40 mmol). The reaction mixture was heated at 80° C. for 16 h and then concentrated. The residue was treated with 1N HCl and extracted with DCM (3×). The organic layer was dried with MgSO4. The crude product was added to an 80 g ISCO silica gel column and was purified with a gradient of 0% to 40% EtOAc/hexanes. The product was obtained as a colorless crystalline solid (3.18 g, 13.02 mmol, 59.2% yield). 1H NMR (CDCl3/400 MHz) δ (ppm) 8.07 (d, 2H), 7.71 (d, 2H), 3.26 (t, 2H), 2.91 (t, 2H), 2.25 (s, 3H); MS m/z: 245.18 (M+1).

Provenance & Evidence