Butyl iodide → 1-Butyl-3-hydroxymethyl-2-pyridone
Reaction equation
[OH:1][CH2:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:17][CH2:18][CH2:19][CH3:20]>CN(C=O)C>[CH2:17]([N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][OH:1])[C:4]1=[O:9])[CH2:18][CH2:19][CH3:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 3-hydroxymethyl-2(1H)-pyridone (7-008-01) (0.63 g) in DMF (15 mL), and to the reaction mixture were added potassium carbonate (1.4 g) and 1-iodobutane (1.86 g). After stirring at 70° C. for 2 h, the solvent was removed. To the residue were added a saturated aqueous solution of ammonium chloride and ethyl acetate, and the organic layer was separated, and then the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained crude product was purified by column chromatography (toluene/ethyl acetone=2/1) to give 1-butyl-3-hydroxymethyl-2-pyridone (7-008-02) (0.56 g, 61%) as an oil.
Workup
- customthe solvent was removed
- additionTo the residue were added a saturated aqueous solution of ammonium chloride and ethyl acetate
- customthe organic layer was separated
- extractionthe aqueous layer was extracted three times with ethyl acetate
- washThe combined organic layers were washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated under reduced pressure
- customThe obtained crude product
- customwas purified by column chromatography (toluene/ethyl acetone=2/1)
Sources & evidence
- ORD record
- ord-0dd9ce93802f4d2a8910aaba3ec7ecc5
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088924B2
Reaction notes
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