Acetophenone → 1-phenyl-3-(pyridin-2-yl)propane-1,3-dione

HRID 2374107Notes

Reaction equation

HRID 2374107 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](OCC)=[O:23]>C1(C)C=CC=CC=1>[C:4]1([C:1](=[O:3])[CH2:2][C:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=2)=[O:23])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 17307Ethyl 2-pyridinecarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 2384481-phenyl-3-(pyridin-2-yl)propane-1,3-dioneYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetophenone (11.6 mL, 99 mmol), was added to a suspension of potassium tert-butoxide (12.34 g 110 mmol) in toluene (150 mL) and stirred under argon. The flask was then charged with ethyl picolinate (13.4 mL, 99 mmol) and the mixture stirred overnight. The toluene was removed by rotary evaporation and 200 mL of both diethylether and deionised water added. With stirring the mixture was acidified with dilute HCl until the ether layer was dark orange˜pH 7). The ether layer was separated, washed with deionised water (3×100 mL), dried over magnesium sulfate and filtered. The solvent was removed and the solid recrystallised from hot ethanol to yield 1-phenyl-3-pyridin-2-ylpropane-1,3-dione (1) as a pale yellow crystalline solid (15.3 g, 69%).

Workup

  1. stirringthe mixture stirred overnight
  2. customThe toluene was removed by rotary evaporation and 200 mL of both diethylether and deionised water
  3. additionadded
  4. stirringWith stirring the mixture
  5. customThe ether layer was separated
  6. washwashed with deionised water (3×100 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed
  10. customthe solid recrystallised from hot ethanol

Sources & evidence

ORD record
ord-8e4e710fffef43a3ae6f0703db5a1274
Source dataset
uspto-grants-2008_12
Patent number
US07462404B2

Reaction notes

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