Aluminium lithium hydride → (5-Amino-2-trifluoromethoxy-phenyl)-methanol

HRID 967621Notes

Reaction equation

HRID 967621 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:11][C:12]([F:15])([F:14])[F:13].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:10][C:8]1[CH:7]=[CH:6][C:5]([O:11][C:12]([F:13])([F:14])[F:15])=[C:4]([CH2:3][OH:2])[CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22061155Methyl 5-amino-2-(trifluoromethoxy)benzoate

Product 1

HCID 22311140(5-Amino-2-trifluoromethoxy-phenyl)-methanolYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-2-trifluoromethoxybenzoic acid methyl ester (3.0 g, 12.8 mmol) was dissolved under nitrogen in THF (20 mL) in a three-necked flask equipped with a thermometer and a separatory funnel. With stirring and ice-cooling lithium aluminium hydride (1 M in THF, 15 mL) was added dropwise over 10 min. Stirring was continued at room temperature for 1 hour, and the reaction mixture was concentrated in vacuo. The residue was suspended in DCM (150 mL) and water (50 mL), and filtered through celite. The filtrate was partitioned between DCM and water. The combined organic phases were washed with water (2×20 mL), dried (magnesium sulphate) and concentrated in vacuo to give 2.47 g of (5-amino-2-trifluoromethoxyphenyl)methanol.

Workup

  1. customequipped with a thermometer and a separatory funnel
  2. additionwas added dropwise over 10 min
  3. stirringStirring
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. filtrationwater (50 mL), and filtered through celite
  6. customThe filtrate was partitioned between DCM and water
  7. washThe combined organic phases were washed with water (2×20 mL)
  8. dry with materialdried (magnesium sulphate)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1e44409d2a341fba5569a7984f0b02e
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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