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Butyl iodide → 1-Butyl-3-hydroxymethyl-2-pyridone

HRID 1994272
Notes
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Reaction equation

HRID 1994272 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 106304823-(Hydroxymethyl)pyridin-2(1H)-one

Product 1

HCID 222664711-Butyl-3-hydroxymethyl-2-pyridoneYield 61.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-hydroxymethyl-2(11)-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

  1. customthe solvent was removed
  2. additionTo the residue were added a saturated aqueous solution of ammonium chloride and ethyl acetate
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe obtained crude product
  9. customwas purified by column chromatography (toluene/ethyl acetone=2/1)

Sources & evidence

ORD record
ord-8fccb6e95997459d95da9a30f35b0601
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07652141B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes