Tetrahydrofuran → 4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl alcohol

HRID 644009Notes

Reaction equation

HRID 644009 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1.C1C[O:32]CC1>>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:10][C:9]=1[CH2:19][CH2:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][OH:32])=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 205966165-Methyl-2-phenyl-4-(2-p-tolyloxy-ethyl)-oxazoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 118338284-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl alcohol

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (61 mL of a 1.0 M solution in THF) is added to a solution of the title A compound, 5-methyl-2-phenyl-4-(2-p-tolyloxy-ethyl)-oxazole (8.22 g, 24.36 mmol) in THF (200 mL) at 0° C. The mixture is stirred at 0° C. for 5 h, then at RT overnight. The reaction mixture is then cooled in an ice-water bath and quenched with saturated aqueous sodium bicarbonate and concentrated under vacuum to remove some of the THF. The residue is extracted with EtOAc, and the resulting organic phase is washed with brine, dried with magnesium sulfate, and concentrated under vacuum to give {4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-methanol as a white solid.

Workup

  1. customat RT
  2. customovernight
  3. temperatureThe reaction mixture is then cooled in an ice-water bath
  4. customquenched with saturated aqueous sodium bicarbonate
  5. concentrationconcentrated under vacuum
  6. customto remove some of the THF
  7. extractionThe residue is extracted with EtOAc
  8. washthe resulting organic phase is washed with brine
  9. dry with materialdried with magnesium sulfate
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-30e8d9c77b27454cadd5cb255631df84
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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