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

HRID 80824Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:20]=[C:19]([CH3:21])[C:14]([C:15]([O:17]C)=[O:16])=[C:13](/[CH:22]=[CH:23]/[CH3:24])[N:12]=1)[CH3:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>O>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:11]1[N:12]=[C:13]2[CH2:22][CH:23]([CH3:24])[O:17][C:15](=[O:16])[C:14]2=[C:19]([CH3:21])[CH:20]=1)[CH3:10]

Participants

Conditions

Temperature: 160 °C

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)+.

Workup

temperatureheating
waitat 140° C. for 2 h
additionThe reaction was then poured
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was then purified with FCC (0-50% EtOAc/heptane)

Sources & evidence

ORD record: ord-7b6ca56ae7704739af5d680fca44f48e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846656B2

Reaction notes

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