Water → 2-Amino-1-(4-benzyloxyphenyl)ethanol

HRID 920531Notes

Reaction equation

HRID 920531 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]([CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)=[O:12])=[N+]=[N-].O.[OH-].[Na+]>C1COCC1>[NH2:7][CH2:10][CH:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 714163332-Azido-1-[4-(benzyloxy)phenyl]ethan-1-one

Product 1

HCID 4239902-Amino-1-(4-benzyloxyphenyl)ethanolYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of LiAlH4 (8.18 g; 215.6 mmol) in THF (100 mL), was added dropwise a solution of 2-azido-1-(4-benzyloxy-phenyl)-ethanone (23.05 g; 86.2 mmol) in THF (200 mL), at 0° C. The mixture was stirred at 0° C. for 20 min. and subsequently 2 hours at RT. Thereafter, water (50 mL), and 2M aqueous NaOH-solution (150 mL) were added consecutively. The formed precipitate was removed by filtration over kieselguhr, and washed with MeOH. The filtrate was concentrated in vacuo and the remaining aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford 2-amino-1-(4-benzyloxy-phenyl)-ethanol (20.10 g)

Workup

  1. customat 0° C
  2. customThe formed precipitate was removed by filtration over kieselguhr
  3. washwashed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. extractionthe remaining aqueous layer was extracted with CH2Cl2
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fadfc1712c64a47a70a42c015dbe04e
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

Loading…