Diethyl Ether → 4-Amino-3-(3,4-dichlorophenyl)-1-butanol

HRID 2294985Notes

Reaction equation

HRID 2294985 reaction equation
CCOCC.[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]([CH2:26][N+:27]([O-])=O)[CH2:21][C:22](OC)=[O:23])[CH:16]=[CH:17][C:18]=1[Cl:19]>O1CCCC1>[NH2:27][CH2:26][CH:20]([C:15]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([Cl:12])[CH:14]=1)[CH2:21][CH2:22][OH:23]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 214725024-Nitro-3-(3,4-dichlorophenyl)butanoic acid methyl ester

Product 1

HCID 97946634-Amino-3-(3,4-dichlorophenyl)-1-butanolYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 1M Et2O solution of LiAlH4 (200 mL, 200 mmol) at 0° C., slowly add the product of Step 2 (14.35 g, 49.1 mmol) dissolved in tetrahydrofuran (THF) (100 mL). Allow the reaction mixture to warm to room temperature and stir for 45 min. After recooling to 0° C., quench the excess LiAlH4 by the careful addition of aqueous saturated Na2SO4 (20 mL). Dry the solution with Na2SO4 and filter. Wash the lithium salts with Et2O (3×300 mL). Concentrate the combined filtrates to give 8.65 g of 4-amino-3-(3,4-dichlorophenyl)-butanol as a white solid (36.9 mmol, 75%).

Workup

  1. customAfter recooling to 0° C.
  2. customquench the excess LiAlH4
  3. additionby the careful addition of aqueous saturated Na2SO4 (20 mL)
  4. dry with materialDry the solution with Na2SO4
  5. filtrationfilter
  6. washWash the lithium salts with Et2O (3×300 mL)
  7. concentrationConcentrate the combined filtrates

Sources & evidence

ORD record
ord-426c452348484a2280bbde998c6fff5d
Source dataset
uspto-grants-1997_11
Patent number
US05691362

Reaction notes

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