4H-pyran-4-one → 4-Methylbenzaldehyde

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

4-Pyranone (2.31 mL, 24.97 mmol) and sulphur (801 mg, 24.97 mmol) were added to a solution of 3-oxo-3-p-tolyl-propionitrile (3.79 g, 23.8 mmol) in ethanol (40 mL) followed by morpholine (2.18 mL, 24.97 mmol) and the reaction heated at 40° C. for 16 hours, The reaction mixture was concentrated in vacuo and the residue purified by flash chromatography on silica eluting with 0-20% ethylacetate/heptanes to afford 12-Amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-yl)-p-tolyl-methanone as a yellow solid (2.2 g, 36% yield). LCMS (2 min acidic) 1.07 min ES+/AP+ 274 (MH+). 1HNMR (400 MHz, CDCl3) δ ppm 2.00-2.03 (m, 2H), 2.42 (s, 3H), 3.80-3.84 (m, 2H), 4.80 (s, 2H), 6.60 (br s, 2H), 7.20 (d, 2H), 7.41 (d, 2H).

Herkunft & Nachweise