2,2,2-Trifluoroethanol → HCID 117839785, compound

HRID 1477624Notes

Reaction equation

HRID 1477624 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].Br[C:10]1[S:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:14]=1.[OH-].[Na+]>C(OCC)(=O)C.O1CCCC1>[F:3][C:4]([F:8])([F:7])[CH2:5][O:6][C:10]1[S:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:14]=1

Participants

7

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 2773502Methyl 2-bromothiazole-5-carboxylate

Product 1

HCID 117839785HCID 117839785, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (5.0 mL) of sodium hydride (465 mg, 11.6 mmol) and 2,2,2-trifluoroethanol (1.70 mL, 23.3 mmol), methyl 2-bromothiazole-5-carboxylate (517 mg, 2.33 mmol) was added and the resultant mixture was stirred at room temperature for 2 hours. After completion of the reaction, 1 M sodium hydroxide aqueous solution was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product of the title compound (444 mg).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0c88d2b9e1e4ee6a181eabc49992a91
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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