Sodium Hydroxide → 2-Amino-1-(1-benzofuran-2-yl)ethan-1-ol

HRID 1388744Notes

Reaction equation

HRID 1388744 reaction equation
C[Si]([C:5]#[N:6])(C)C.[CH:7]([C:9]1[O:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[CH:13]=1)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>CCOCC.[I-].[Zn+2].[I-].O>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[CH:13]=[C:9]1[CH:7]([OH:8])[CH2:5][NH2:6]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 613412-BenzofurancarboxaldehydeHCID 82115Trimethylsilyl cyanideHCID 21226445Aluminium lithium hydride

Product 1

HCID 128143572-Amino-1-(1-benzofuran-2-yl)ethan-1-olYield 65.2%

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

Trimethylsilylcyanide (1.63 g, 2 ml) was added to a solution of 2-formylbenzofuran (2.0 g), (prepared as described in French Pat. No. 1.537.206) and a trace of zinc iodide in dry ether (50 ml) at 0° under nitrogen. The reaction mixture was stirred under nitrogen at ambient temperature for 10 h. This solution was then added dropwise to a suspension of lithium aluminium hydride (0.63 g) in dry ether under nitrogen. The mixture was heated under reflux for 1 h at the end of the addition. The reaction mixture was cooled; water (0.63 ml), 2 M sodium hydroxide (0.63 ml) and more water (1.89 ml) added, the reaction mixture filtered, the residue washed with chloroform and the combined solvents evaporated to give 2-(2-benzofuranyl)-2-hydroxyethanamine, (1.58 g).

Workup

  1. custom(prepared
  2. customat 0°
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 1 h at the end of the addition
  5. temperatureThe reaction mixture was cooled
  6. filtrationthe reaction mixture filtered
  7. washthe residue washed with chloroform
  8. customthe combined solvents evaporated

Sources & evidence

ORD record
ord-3e20dda27f7145ecaac4dc28a09030f1
Source dataset
uspto-grants-1984_02
Patent number
US04432993

Reaction notes

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