Potassium tert-butoxide → HCID 22033035, compound

HRID 1665854Notes

Reaction equation

HRID 1665854 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:26])[CH:10]([O:17]C(=O)C2C=CC=CC=2)[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:5][CH:4]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[OH:17][CH:10]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[C:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)=[O:26]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 57826339HCID 57826339, compound

Product 1

HCID 22033035HCID 22033035, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of benzoic acid 2-(4-methoxy-phenyl)-2-oxo-1-pyridin-3-yl-ethyl ester (1.21 g, 3.38 mmol) prepared in Step 2 in 3 mL of tert-butanol was slowly added 6.5 mL of 1.0 M potassium tert-butoxide under nitrogen atmosphere. The resulting mixture was stirred for 1 day and concentrated under reduced pressure to remove the solvent. The concentrate was diluted with 50 mL of ethyl acetate and 50 mL of water to dissolve salts, followed by separation of layers. The obtained organic layer was successively washed twice with 50 mL of a brine solution. The organic layer was dried over magnesium sulfate, filtered, concentrated under reduced pressure and purified by silica gel column chromatography, to give 356 mg (yield: 49%) of 2-hydroxy-1-(4-methoxy-phenyl)-2-pyridin-3-yl-ethanone of the following formula.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the solvent
  3. additionThe concentrate was diluted with 50 mL of ethyl acetate and 50 mL of water
  4. dissolutionto dissolve salts
  5. customfollowed by separation of layers
  6. washThe obtained organic layer was successively washed twice with 50 mL of a brine solution
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f09a50674ac440182f80272fb339bb8
Source dataset
uspto-grants-2011_10
Patent number
US08039634B2

Reaction notes

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