HCID 18786133, compound → HCID 18786135, compound

HRID 1107872Notes

Reaction equation

HRID 1107872 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:11]([CH:12]([OH:18])[CH2:13][NH:14]CC=C)=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].C(#N)C.O>[CH3:1][C:2]1[O:3][C:4]2[C:11]([CH:12]([OH:18])[CH2:13][NH2:14])=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7]

Participants

4

Reactant 1

HCID 18786133HCID 18786133, compound

Product 1

HCID 18786135HCID 18786135, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 18373917Acetonitrile--water (1/1)Solvent3×

Procedure

1 g (4 mmol) of 2,3-dimethyl-7-(2-allylamino-1-hydroxyethyl)benzofuran, 85 mg (0.092 mmol) of Wilkinson's catalyst (tris(triphenylphosphine)rhodium(I)) and 25 ml of an acetonitrile/water (84/16) mixture are introduced into a 100 ml three-necked flask equipped with a distillation system and a 50 ml dropping funnel. 30 ml of the same acetonitrile/water (84/16) mixture are placed in the dropping funnel. The solution is stirred at reflux, under a nitrogen stream, for 1 h 30, small amounts of acetonitrile/water (84/16) mixture being added regularly in order to replace the solvent distilled off. The mixture is subsequently concentrated under vacuum and the residue is purified by column chromatography (elution solvent: 90/10 dichloromethane/methanol) and then dried in a desiccator under vacuum over phosphorus pentoxide. 354 mg of 2,3-dimethyl-7-(2-amino-1-hydroxyethyl)benzofuran are obtained--M.p.: 73° C.

Workup

  1. customequipped with a distillation system
  2. temperatureat reflux, under a nitrogen stream
  3. distillationdistilled off
  4. concentrationThe mixture is subsequently concentrated under vacuum
  5. customthe residue is purified by column chromatography (elution solvent: 90/10 dichloromethane/methanol)
  6. dry with materialdried in a desiccator under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-55dfe678bff04068bedcddd7a0a7459c
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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