Acetate → HCID 22033441, compound

HRID 1792319Notes

Reaction equation

HRID 1792319 reaction equation
O[CH:2]([C:11]1(OC)[CH:16]=[CH:15][N:14]=[CH:13][CH2:12]1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:19]([O-:22])(=O)C.[C:23]([O-])(O)=[O:24].[Na+].[NH4+].[Cl-]>O1CCCC1.CN(C=O)C>[CH3:23][O:24][C:8]1[CH:7]=[C:6]2[C:5]([C:3](=[O:4])[CH:2]([C:11]3[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=3)[CH2:19][O:22]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 175AcetateHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 69590077HCID 69590077, compound

Product 1

HCID 22033441HCID 22033441, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-hydroxy-4-methoxy-2-(4-pyridyl)acetophenone (3.51 g, 14.4 mmol) in tetrahydrofuran (30 ml) were added under ice-cooling dry acetate (2.72 ml, 28.8 mmol) and a solution of N,N,N′,N′-tetramethyl-diaminomethane (1.96 ml, 14.4 mmol) in DMF (10 ml), which was then stirred for 30 minutes. After the reaction was completed, the reaction solution was neutralized under ice-cooling using saturated aqueous NaHCO3 solution, extracted with ethyl acetate, and washed with saturated saline solution. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in tetrahydrofuran (20 mg), tetta-n-butylammonium fluoride (11.0 mmol/g, 0.144 mg, 0.144 mmol) was added thereto under ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, saturated aqueous NH4Cl solution was added to the reaction solution, which was then extracted with ethyl acetate and washed with saturated saline solution. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate=1:2) to give 7-methoxy-3-(4-pyridyl)chroman-4-one (2.02 g, yield 55%).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated saline solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. dissolutionThe residue was dissolved in tetrahydrofuran (20 mg)
  7. temperatureunder ice-cooling
  8. extractionwas then extracted with ethyl acetate
  9. washwashed with saturated saline solution
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a619bff754cd4f39b2201f36aedd1f84
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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