Hydrochloric Acid → 1-(4-Methyl-3-pyridinyl)ethanone
Reaction equation
[CH3:1][C:2]1[C:7]([C:8]#N)=[CH:6][N:5]=[CH:4][CH:3]=1.Cl.[OH-:11].[Na+].[CH3:13]COCC>>[C:8]([C:7]1[CH:6]=[N:5][CH:4]=[CH:3][C:2]=1[CH3:1])(=[O:11])[CH3:13]Participants
5
Conditions
- Temperature
- 50 °C
Procedure
To a solution of compound (14)(2.0 g, 16.9 mmol) in ether (13 ml) was added a methylmagnesium iodide-ether solution (18.2 ml, 27.4 mmol) under ice-cooling. The reaction mixture was heated to 50° C. and stirred overnight. The reaction mixture was again ice-cooled and 5% hydrochloric acid (400 ml) was added. The reaction mixture was neutralized with a 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was combined and dried (MgSO4) and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give a yellow oil (1.26 g, 55%).
Workup
- temperaturecooling
- temperaturecooled
- extractionextracted with ethyl acetate
- dry with materialdried (MgSO4)
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-ad628cd7b7f442f5bf02b5d3e4a73df9
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067537B2
Reaction notes
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