Sodium Hydroxide → 2-Amino-1-(3-fluoro-4-methoxyphenyl)ethan-1-ol

HRID 851181Notes

Reaction equation

HRID 851181 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].C[Si]([C:16]#[N:17])(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>CCOCC.[I-].[Zn+2].[I-].O>[OH:6][CH:5]([C:4]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([F:1])[CH:3]=1)[CH2:16][NH2:17]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 676963-Fluoro-p-anisaldehydeHCID 82115Trimethylsilyl cyanideHCID 21226445Aluminium lithium hydride

Product 1

HCID 130796452-Amino-1-(3-fluoro-4-methoxyphenyl)ethan-1-ol

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent4×

Procedure

To a solution of 3-fluoro-4-methoxybenzaldehyde (5.0 g) in dry ether (100 ml) containing a catalytic amount of zinc iodide was added dropwise a solution of trimethylsilyl cyanide (5 ml) in dry ether. After stirring at room temperature overnight the ether solution was added to an ice-cooled suspension of lithium aluminium hydride (4.0 g) in dry ether (100 ml) under nitrogen. On completion of this addition this mixture was stirred at room temperature for 30 minutes and then boiled under reflux for 1 hour. After boiling in ice this mixture was treated with water (4 ml), 2 N sodium hydroxide solution (4 ml) and water (12 ml) and this resulting suspension was filtered and dried (MgSO4). Evaporation of the solvent gave a light green oil (3.9 g) which was used without further purification.

Workup

  1. temperaturecooled
  2. additionOn completion of this addition this mixture
  3. temperatureunder reflux for 1 hour
  4. filtrationthis resulting suspension was filtered
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e1789cd1291446489cd8f004002eb84d
Source dataset
uspto-grants-1983_05
Patent number
US04382958

Reaction notes

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