Hydrochloric Acid → HCID 58765710, compound

HRID 860607Notes

Reaction equation

HRID 860607 reaction equation
C([O:3][C:4](=O)[CH:5]([C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH:22]([CH3:24])[CH3:23])[CH3:6])C.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C(OCC)(=O)C>[CH:22]([C:8]1[N:9]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=2)[O:11][C:7]=1[CH:5]([CH3:6])[CH2:4][OH:3])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 69057069HCID 69057069, compound

Product 1

HCID 58765710HCID 58765710, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propionic acid ethyl ester (1.11 g, 3.12 mmol) and tetrahydrofuran (50 mL) are cooled to 0° C. Lithium aluminum hydride (0.24 g, 6.25 mmol) is added and the resulting mixture is stirred 20 hr at room temperature. The mixture is cooled to 0° C. and 1M aqueous hydrochloric acid (50 mL) is carefully added. The mixture is then diluted with ethyl acetate (100 mL) and the layers are separated. The aqueous layer is washed with ethyl acetate (100 mL) and the organic ishes are combined, washed with water and brine (50 mL each), dried over anhydrous magnesium sulfate, filtered and concentrated to constant weight to give 2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-1-ol as a pale orange oil, 1.03 g, 100%. MS (M++1) 314.

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. customthe layers are separated
  3. washThe aqueous layer is washed with ethyl acetate (100 mL)
  4. washwashed with water and brine (50 mL each)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to constant weight

Sources & evidence

ORD record
ord-02d1121416b4436da2b4b2a316523d69
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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