Hydrochloric Acid → HCID 58765710, compound

HRID 490730Notes

Reaction equation

HRID 490730 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 washes 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. The following compound is made in similar manner:

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-0d4c5541198a4735972bcb24a8d3f18e
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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