2,2,2-Trifluoroethanol → 1-{4-[5-Phenyl-4-(2,2,2-trifluoroethoxymethyl)-oxazol-2-yl]-piperidin-1-yl}-ethanone

HRID 2288959Notes

Reaction equation

HRID 2288959 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH2:15]2)[O:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].[F:25][C:26]([F:30])([F:29])[CH2:27][OH:28]>O>[C:8]1([C:7]2[O:6][C:5]([CH:14]3[CH2:19][CH2:18][N:17]([C:20](=[O:22])[CH3:21])[CH2:16][CH2:15]3)=[N:4][C:3]=2[CH2:2][O:28][CH2:27][C:26]([F:30])([F:29])[F:25])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 14798Sodium HydroxideHCID 187004361-[4-(4-Chloromethyl-5-phenyl-oxazol-2-yl)-piperidin-1-yl]ethanone

Product 1

HCID 187004391-{4-[5-Phenyl-4-(2,2,2-trifluoroethoxymethyl)-oxazol-2-yl]-piperidin-1-yl}-ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
72 °C

Procedure

A solution of 1-[4-(4-chloromethyl-5-phenyl-oxazol-2-yl)-piperidin-1-yl]ethanone (30 g, 94.1 mmol), prepared as in Intermediate 3B, in 2,2,2-trifluoroethanol (450 ml) is treated with a solution of NaOH (56 g, 1412 mmol) in water (150 ml). After heating at 72° C. for 15 hours, the reaction mixture is concentrated. The residue is partitioned between EtOAc and water. The aqueous phase is reextracted once with EtOAc, and the combined organic phases are washed with saturated brine, dried (Na2SO4) and concentrated to afford 1-{4-[5-phenyl-4-(2,2,2-trifluoroethoxymethyl)-oxazol-2-yl]-piperidin-1-yl}-ethanone.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. customThe residue is partitioned between EtOAc and water
  3. washthe combined organic phases are washed with saturated brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7e623cfd335e4f6d8e6ec1f823c663cb
Source dataset
uspto-grants-2000_07
Patent number
US06090825

Reaction notes

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