反应详情

温度

100 °C

A mixture of 6-bromo-4-oxo-spiro[chromane-2,4′-piperidine]-1′-carboxylic acid tert-butyl ester (1.04 g, 2.62 mmol), Pd(OAc)2 (59 mg, 0.262 mmol), PPh3 (137 mg, 0.52 mmol), TEA (0.73 ml, 5.2 mmol), methyl acrylate (0.47 ml, 5.2 mmol) in dry DMF (10 ml) was heated at 100° C. for 8 h. The mixture was cooled down to RT, filtered on a celite pad and washed with AcOEt (100 ml). The filtrate was washed with NH4Cl and saturated NaHCO3 solution and brine. The organic phase was dried over Na2SO4 and evaporated under vacuum. The crude residue was purified by column chromatography (eluent: hexane/AcOEt 90:10 to 70:30) to give (E)-3-{1′-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (594 mg) as a light yellow solid.

1. temperatureThe mixture was cooled down to RT
2. filtrationfiltered on a celite pad
3. washwashed with AcOEt (100 ml)
4. washThe filtrate was washed with NH4Cl and saturated NaHCO3 solution and brine
5. dry with materialThe organic phase was dried over Na2SO4
6. customevaporated under vacuum
7. customThe crude residue was purified by column chromatography (eluent: hexane/AcOEt 90:10 to 70:30)