Ethyl Acetate → HCID 10353064, compound

HRID 2101213Notes

Reaction equation

HRID 2101213 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:14](=[O:17])([O-])O.[Na+].[CH3:19][CH2:20]OC(C)=O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:4]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=[C:2]([CH2:19][CH2:20][CH:14]=[O:17])[CH:3]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 885421,1'-Biphenyl, 3-iodo-HCID 516892Sodium Bicarbonate

Product 1

HCID 10353064HCID 10353064, compoundYield 83%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 3-iodo-1,1′-biphenyl (0.964 g, 3.44 mmol) and tetrabutylammonium chloride (0.956 g, 3.44 mmol) in dry DMF (3 mL) was added alkyl alcohol (0.351 mL, 5.16 mmol), sodium hydrogencarbonate (0.723 g, 8.60 mmol), and palladium(II) acetate (31 mg, 0.14 mmol), and the mixture was stirred at room temperature for 18 h. The reaction mixture was then diluted with EtOAc and the solid material filtered off (Celite). The filtrate was washed with water three times, dried (Na2SO4) and concentrated. Flash chromatography (heptan/tert-butyl methyl ether, 4:1) of the residue gave 3-(1,1′-biphenyl-3-yl)propanal (0.601 g, 83%).

Workup

  1. filtrationthe solid material filtered off (Celite)
  2. washThe filtrate was washed with water three times
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4a5b214f9338435bb40e4697392b2a78
Source dataset
uspto-grants-2009_08
Patent number
US07572817B2

Reaction notes

Loading…