Aluminium lithium hydride → HCID 69061921, compound

HRID 490723Notes

Reaction equation

HRID 490723 reaction equation
C([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH:21]([CH3:23])[CH3:22])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.Cl>[CH:21]([C:7]1[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][CH:12]=2)[O:10][C:6]=1[CH2:4][OH:3])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69053962HCID 69053962, compound

Product 1

HCID 69061921HCID 69061921, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Isopropyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid ethyl ester (0.53 g, 1.62 mmol) is stirred in tetrahydrofuran (25 mL) at 0° C. Lithium aluminum hydride (0.122 g, 3.23 mmol) is added and the mixture is stirred 18 hr at room temperature. The mixture is diluted carefully with 1M aqueous hydrochloric acid (10 mL), and the product is extracted with ethyl acetate (three 75 mL portions). The extracts are combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford [4-Isopropyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-methanol as a white solid, 0.46 g, 100%. MS (M++1) 286

Workup

  1. extractionthe product is extracted with ethyl acetate (three 75 mL portions)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0c6330c00ba844d69b234955fe50c2b0
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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