Sodium Hydroxide → HCID 57655961, compound

HRID 911266Notes

Reaction equation

HRID 911266 reaction equation
[OH-].[Na+].[CH3:3][C:4]([CH3:24])([CH3:23])[C:5](=[O:22])[CH2:6][O:7][C:8]1[CH:21]=[CH:20][C:11]([CH2:12][NH:13]C(=O)C(F)(F)F)=[CH:10][CH:9]=1>CO>[CH3:3][C:4]([CH3:24])([CH3:23])[C:5](=[O:22])[CH2:6][O:7][C:8]1[CH:21]=[CH:20][C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57655997HCID 57655997, compound

Product 1

HCID 57655961HCID 57655961, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 5N aqueous NaOH (15 mL) to a solution of N-[4-(3,3-dimethyl-2-oxo-butoxy)-benzyl]-2,2,2-trifluoro-acetamide (552 mg, 1.74 mmol) in methanol (0 mL) and stir for 2 h at ambient temperature. Extract the mixture with DCM three times. Dry the combined organic extracts over Na2SO4, filter and concentrate. Purify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (92:8) to give the title compound as a colorless oil (337 mg, 87%). MS (ES+) m/z: 205 M+H−NH3)+.

Workup

  1. extractionExtract the mixture with DCM three times
  2. dry with materialDry the combined organic extracts over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (92:8)

Sources & evidence

ORD record
ord-67801d20918b479ea8b1d463e01ce67d
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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