4-Methyl-1-penten-3-ol → 4-Methyl-1-pyridin-3-yl-pentan-3-one

HRID 23448

Reaction equation

HRID 23448 reaction equation
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:8][CH:9]([CH3:14])[CH:10]([OH:13])[CH:11]=[CH2:12].C(=O)(O)[O-].[Na+].N1CCCC1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:8][CH:9]([CH3:14])[C:10](=[O:13])[CH2:11][CH2:12][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 209294-Methyl-1-penten-3-olHCID 31268PyrrolidineHCID 707143-IodopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 225730904-Methyl-1-pyridin-3-yl-pentan-3-one

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to General Method 4a using 3-iodo-pyridine (36.6 mmol), 4-methyl-1-penten-3-ol (54.9 mmol), tetrabutyl ammonium chloride (36.6 mmol), sodium bicarbonate (91.5 mmol), pyrrolidine (˜1.5 mL), DMF (15 mL), and palladium acetate (0.51 g). The title compound was flash chromatographed eluting with EtOAc:CH2Cl2:hexane 50:25:25.

Workup

  1. customThe title compound was prepared
  2. customchromatographed
  3. washeluting with EtOAc:CH2Cl2:hexane 50:25:25

Sources & evidence

ORD record
ord-248416efd0a649f9b7efec92ff948b0f
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Linked notes

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