Sodium borohydride → 1-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethanol

HRID 474614Notes

Reaction equation

HRID 474614 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH:15]([OH:17])[CH3:16])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:18]([F:19])([F:20])[F:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 677750201-[4-(4-Chloro-3-trifluoromethylphenoxy)-phenyl]-ethanone

Product 1

HCID 677755811-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethanolYield 73.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 1-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethanone (3.12 g, 9.91 mmol) in Ethanol (60 ml), was added NaBH4 (0.450 g, 11.90 mmol). The solution was stirred at room temperature under nitrogen for 1 h. After removing the solvent, the residue was dissolved in DCM, then washed with water twice. The solvent was dried over Na2SO4, concentrated to afford the title compound (2.3 g, 73.2% yield) as light yellow oil. LCMS: rt=3.63 min, [M+H+]=299

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water twice
  4. dry with materialThe solvent was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f8f575506f5e455bbe2c71a5a80c487d
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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