Tributylstannane → HCID 22262058, compound

HRID 1610763Notes

Reaction equation

HRID 1610763 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][C:11]([CH3:13])=[CH2:12].N(C(C)(C)C#N)=NC(C)(C)C#N.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:12][C:11]1([CH3:13])[C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=2[O:9][CH2:10]1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 334095HCID 334095, compound

Product 1

HCID 22262058HCID 22262058, compoundYield 110.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-bromo-4-methyl-1-[(2-methyl-2-propenyl)oxy]benzene (5.0 g, 20.7 mmol) in toluene (100 ml) were added 2,2′-azobisisobutyronitrile (1.45 g, 8.8 mmol) and tri-n-butyltin hydride (8.34 ml, 31 mmol), and the mixture was heated under reflux overnight. After completion of the reaction, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0, 50:1) to give 3,3,5-trimethyl-2,3-dihydro-1-benzofuran (3.70 g, 100%) as a colorless transparent oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0, 50:1)

Sources & evidence

ORD record
ord-50dc93ea35f742898aceb3aca3d48cff
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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