4-Methyl-1-penten-3-ol → 1-Furan-3-yl-4-methyl-pentan-3-one

HRID 23449

Reaction equation

HRID 23449 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.[CH3:7][CH:8]([CH3:13])[CH:9]([OH:12])[CH:10]=[CH2:11].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[O:4]1[CH:5]=[CH:6][C:2]([CH2:11][CH2:10][C:9](=[O:12])[CH:8]([CH3:13])[CH3:7])=[CH:3]1

Participants

7

Reactant 3

HCID 209294-Methyl-1-penten-3-olHCID 891643-BromofuranHCID 516892Sodium Bicarbonate

Product 1

HCID 225730251-Furan-3-yl-4-methyl-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-bromofuran (17 mmol), 4-methyl-1-penten-3-ol (25.5 mmol), tetrabutyl ammonium chloride (17 mmol), sodium bicarbonate (42.5 mmol), DMF (15 mL), and palladium acetate (0.9 mmol). The title compound was flash chromatographed eluting with EtOAc:hexane (5:95 to 10:90).

Workup

  1. customThe title compound was prepared
  2. customchromatographed
  3. washeluting with EtOAc:hexane (5:95 to 10:90)

Sources & evidence

ORD record
ord-a211614668054fd4ad48f16105273d61
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Linked notes

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