2-Tert-butyl-5-methyl-4-oxazoleacetic acid → 2-(2-Tert-butyl-5-methyl-oxazol-4-yl)-ethanol

HRID 2215192Notes

Reaction equation

HRID 2215192 reaction equation
[C:1]([C:5]1[O:6][C:7]([CH3:14])=[C:8]([CH2:10][C:11](O)=[O:12])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([C:5]1[O:6][C:7]([CH3:14])=[C:8]([CH2:10][CH2:11][OH:12])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 132829732-Tert-butyl-5-methyl-4-oxazoleacetic acid

Product 1

HCID 115792322-(2-Tert-butyl-5-methyl-oxazol-4-yl)-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13.77 g of the above prepared (2-tert-butyl-5-methyl-oxazol-4-yl)-acetic acid (69.8 mmol) was dissolved in 460 ml of abs. THF and treated at 0° C. with 174.5 ml of 1M BH3,THF (2.5 eq.). The reaction mixture was then kept over night at ambient temperature. Careful quenching with ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents left a crude product which was refluxed for 60 Min. in MeOH to liberate quantitatively the free alcohol. Removing of the solvent and flash chromatography (SiO2, AcOEt) delivered finally 9.23 g of the title compound as colorless oil.

Workup

  1. dissolutionwas dissolved in 460 ml of abs
  2. waitThe reaction mixture was then kept over night at ambient temperature
  3. customCareful quenching with ice, twofold extraction with AcOEt
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  6. waitleft a crude product which
  7. temperaturewas refluxed for 60 Min
  8. customRemoving of the solvent and flash chromatography (SiO2, AcOEt)

Sources & evidence

ORD record
ord-80744070a3724589ba572d31636334d5
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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