Aluminium lithium hydride → HCID 69061921, compound

HRID 860600Notes

Reaction equation

HRID 860600 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-eb47c75f35b74ec08497379b5e373962
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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