Reaction #168006

Reaction equation

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

Solvents

H2O

H2O

Conditions

Workup

1. 1
   Temperatureheating
2. 2
   workup.WAITat 140° C. for 2 h
3. 3
   workup.ADDITIONThe reaction was then poured
4. 4
   Extractionextracted with EtOAc
5. 5
   WashThe organic layer was washed with brine
6. 6
   Dryingdried over Na2SO4
7. 7
   Concentrationconcentrated
8. 8
   OtherThe residue was then purified with FCC (0-50% EtOAc/heptane)

Procedure

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)+.

Source