Water → N-Ethyl-2-(4-ethynyl-phenyl)-propionamide

HRID 330825Notes

Reaction equation

HRID 330825 reaction equation
[CH2:1]([NH:3][C:4](=[O:19])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si](C)(C)C)=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH2:1]([NH:3][C:4](=[O:19])[CH:5]([C:7]1[CH:8]=[CH:9][C:10]([C:13]#[CH:14])=[CH:11][CH:12]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 66693050N-Ethyl-2-(4-trimethylsilanylethynyl-phenyl)-propionamide

Product 1

HCID 86669567N-Ethyl-2-(4-ethynyl-phenyl)-propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 9.73 g (35.6 mmol) N-ethyl-2-(4-trimethylsilanylethynyl-phenyl)-propionamide (XVI.1) in 400 mL THF, an aqueous solution of 24.81 g (71.2 mmol) tetra-n-butyl-ammonium fluoride (75%) is added. The mixture is stirred at rt for 45 min. After that time, water is added and the mixture is extracted with EtOAc twice. The combined organic layers are washed with brine and dried over sodium sulphate. The solvent is evaporated and the residue is purified by column chromatography (silicia gel; EtOAc/heptane, gradient 50% to 80%) to yield the desired product.

Workup

  1. extractionthe mixture is extracted with EtOAc twice
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent is evaporated
  5. customthe residue is purified by column chromatography (silicia gel; EtOAc/heptane, gradient 50% to 80%)

Sources & evidence

ORD record
ord-d8753cf9d133425d9d469e70923990a9
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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