Borane;tetrahydrofuran → 2-(5-Methyl-2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)ethanol

HRID 479133Notes

Reaction equation

HRID 479133 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][C:18](O)=[O:19].B.C1COCC1>C1COCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:17][CH2:18][OH:19]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 18003528[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-acetic acid

Product 1

HCID 105881722-(5-Methyl-2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.33 g of the above prepared [5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-acetic acid (25.7 mmol) was dissolved in 120 ml of abs. THF and treated at 0° C. with 64 ml 1M BH3THF (2.5 eq.). The reaction mixture was then kept over night et ambient temperature. Careful quenching with MeOH and ice, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents left a crude product which was refluxed for 30 min. in MeOH to liberate quantitatively the free alcohol. Flash chromatography (SiO2, hexane/AcOEt=7/3) delivered finally 6.38 g of the title compound as off-white crystals.

Workup

  1. dissolutionwas dissolved in 120 ml of abs
  2. waitThe reaction mixture was then kept over night
  3. customet ambient temperature
  4. customCareful quenching with MeOH and ice, twofold extraction with AcOEt
  5. washwashing with water and brine
  6. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  7. waitleft a crude product which
  8. temperaturewas refluxed for 30 min. in MeOH

Sources & evidence

ORD record
ord-519428e750db4619a9541cf59b7bcaf4
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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