反応 #168006

反応方程式

NaHCO3

(E)-methyl 6-(2,6-diethylphenyl)-4-methyl-2-(prop-1-enyl)nicotinate

TFA

TFA

→

2-(2,6-diethylphenyl)-4,7-dimethyl-7,8-dihydro-5H-pyrano[4,3-b]pyridin-5-one

溶媒

H2O

H2O

反応条件

後処理

1. 1
   温度heating
2. 2
   workup.WAITat 140° C. for 2 h
3. 3
   workup.ADDITIONThe reaction was then poured
4. 4
   抽出extracted with EtOAc
5. 5
   洗浄The organic layer was washed with brine
6. 6
   乾燥dried over Na2SO4
7. 7
   濃縮concentrated
8. 8
   その他The residue was then purified with FCC (0-50% EtOAc/heptane)

実験手順

A mixture of (E)-methyl 6-(2,6-diethylphenyl)-4-methyl-2-(prop-1-enyl)nicotinate (150 mg, 0.464 mmol), H2O (0.17 mL, 9.28 mmol) and TFA (2.9 mL, 37.1 mmol) was heated in a microwave reactor at 160° C. for 30 min. Starting materal was observed. Additional TFA (0.5 mL) and H2O (0.05 mL) were added and heating continued at 160° C. for 45 min and then at 140° C. for 2 h. The reaction was then poured into sat NaHCO3 and extracted with EtOAc. The organic layer was washed with brine and then dried over Na2SO4 and concentrated. The residue was then purified with FCC (0-50% EtOAc/heptane) to provide 2-(2,6-diethylphenyl)-4,7-dimethyl-7,8-dihydro-5H-pyrano[4,3-b]pyridin-5-one. MS (ESI+) m/z 310.3 (M+H)+.

出典