Ethanol → HCID 12369310, compound

Participants

Reaction Conditions

Reaction Steps

In a sealable vial were added nicotinaldehyde (4.7 g, 43.9 mmol), triethylamine (12.17 mL, 87 mmol), but-3-en-2-one (3.97 mL, 43.7 mmol), and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium bromide (2.202 g, 8.73 mmol) in ethanol (10 mL). The reaction mixture was heated at 80° C. for 16 h. The reaction was then concentrated. The residue was treated with 1N HCl and extracted with DCM (3×20 mL). The organic layer was dried with Na2SO4. The crude product was added to a 80 g ISCO silica gel column and was purified with a gradient of 0% to 100% ethyl acetate in hexanes. Collection and concentration of pertinent fractions resulted in isolation of 1-(pyridin-2-yl)pentane-1,4-dione (4.5 g, 58%) as a tan liquid.

Provenance & Evidence