Tributylstannane → 1-(1-Benzofuran-3-yl)ethan-1-one

HRID 748660

Reaction equation

HRID 748660 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10](=[O:13])[CH2:11]Br)=[CH:2]1.C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10](=[O:13])[CH3:11])=[CH:2]1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 27765801-(Benzofuran-3-yl)-2-bromoethanone

Product 1

HCID 112866121-(1-Benzofuran-3-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-benzofuran-3-yl-2-bromo-ethanone (Intermediate I1) (commercially available from Maybridge) (2.1 g, 8.8 mmol) in toluene at reflux was treated with tributyltin hydride (2.9 mL, 10.6 mmol) and 2,2′-azobisisobutyronitrile (AIBN, catalyst) for 2 h. The mixture was cooled to rt and concentrated onto silica gel under reduced pressure. The product was eluted from a column of silica gel with 5% EtOAc: hexane to give 1-benzofuran-3-yl-ethanone (Intermediate I2) as an oil, 1.45 g (99%).

Workup

  1. concentrationconcentrated onto silica gel under reduced pressure
  2. washThe product was eluted from a column of silica gel with 5% EtOAc

Sources & evidence

ORD record
ord-c0c8f0438cd048dca0467085068bb4a6
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Linked notes

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