3,4-Dimethylpyridine → 1-(2-Furyl)-2-(3-methylpyridin-4-yl)ethanone
Reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](OCC)=[O:15].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[Cl-].[NH4+]>C1COCC1>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=[O:15])[CH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH3:1]Participants
Procedure
3,4-Dimethylpyridine (2.25 mL, 20.0 mmol) and ethyl furan-2-carboxylate (5.02 mL, 40.0 mmol) were dissolved in THF (20 mL), and at 0° C., a 1.0 mol/L solution of lithium hexamethyldisilazide in THF (40.0 mL, 40.0 mmol) was added dropwise thereto, followed by stirring at room temperature for 1.5 hours. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed successively with a saturated aqueous solution of ammonium chloride and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:2) to afford 1-(2-furyl)-2-(3-methylpyridin-4-yl)ethanone (3.34 g, 16.6 mmol).
Workup
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed successively with a saturated aqueous solution of ammonium chloride
- dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled away under reduced pressure
- customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:2)
Sources & evidence
- ORD record
- ord-da0d2e2669094aaaabbc796aa47f37bc
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420827B2
Reaction notes
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