Ammonium Chloride → HCID 71294388, compound

HRID 1747539Notes

Reaction equation

HRID 1747539 reaction equation
[Si]([O:8][CH:9]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20](=[O:22])[CH3:21])[CH:15]=1)[C:10]([F:13])([F:12])[F:11])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>C1COCC1>[F:13][C:10]([F:11])([F:12])[CH:9]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20](=[O:22])[CH3:21])[CH:15]=1)[OH:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 71293874HCID 71293874, compound

Product 1

HCID 71294388HCID 71294388, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (6 mL) was dissolved 1-(4-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl)pyridin-2-yl)ethanone (645 mg, 1.93 mmol) obtained in Step 3. Tetrabutylammonium fluoride (1.0 mol/L solution in THF, 0.556 mL, 0.556 mmol) was added and the mixture was stirred at room temperature for 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture. Extraction with ethyl acetate and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give 1-(4-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-2-yl)ethanone (406 mg, 96% yield).

Workup

  1. extractionExtraction with ethyl acetate
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvent in the filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-4799ce31e7cb46f3aecd584caa4f0f93
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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