Selenium Dioxide → Ethyl 2-formylnicotinate

HRID 2308289Notes

Reaction equation

HRID 2308289 reaction equation
[CH3:1][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Se](=O)=[O:14]>O1CCOCC1.O>[C:4]([C:3]1[C:2]([CH:1]=[O:14])=[N:12][CH:11]=[CH:10][CH:9]=1)([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 74401Ethyl 2-methylnicotinate

Product 1

HCID 15639417Ethyl 2-formylnicotinateYield 50.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of ethyl 2-methylnicotinate (1.657 g, 10.0 mmol) in 1,4-dioxane (10 mL) and water (1 mL) was added selenium dioxide (1.568 g, 14.1 mmol) and the resultant mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (3:1 hexanes/ethyl acetate) and provided the title compound (0.90 g, 50%) as a yellow oil. 1H NMR (CDCl3) δ 1.41 (t, 3H, J=7.5 Hz), 4.45 (q, 2 H; J=7.5 Hz), 7.56 (dd, 1H, J=6.0, 6.0 Hz), 8.11 (dd, 1H, J=6.0, 1.0 Hz), 8.87 (dd, 1H, J=6.0, 1.0 Hz), 10.34 (s, 1H).

Workup

  1. temperatureto reflux overnight
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (3:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-d73942be733a413a820e03677319a8cc
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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