Ethyl Acetate → N-Ethyl-2-(4-trimethylsilanylethynyl-phenyl)-propionamide

HRID 330824Notes

Reaction equation

HRID 330824 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[CH2:7]([NH:9][C:10](=[O:20])[CH:11]([C:13]1[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=1)[CH3:12])[CH3:8].CCOC(C)=O>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH2:7]([NH:9][C:10](=[O:20])[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:15][CH:14]=1)[CH3:12])[CH3:8]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 66693450N-Ethyl-2-(4-iodo-phenyl)-propionamide

Product 1

HCID 66693050N-Ethyl-2-(4-trimethylsilanylethynyl-phenyl)-propionamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To 4.90 g (49.9 mmol) trimethylsilylacetylene in 450 mL acetonitrile are added 12.1 g (39.9 mmol) N-ethyl-2-(4-iodo-phenyl)-propionamide (IV.1) under argon, followed by 1.68 g (2.40 mmol) Pd(PPh3)2Cl2 as catalyst, 0.23 g (1.20 mmol) copper(I)iodide and 11.1 mL (80 mmol) TEA as base. The mixture is stirred at rt for 2.5 h. After that time, EtOAc is added and the organic layer is washed with saturated ammonium chloride solution and brine. The organic layer is separated, dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silicia gel; EtOAc/heptane, gradient 50% to 80%) to yield the desired product.

Workup

  1. washthe organic layer is washed with saturated ammonium chloride solution and brine
  2. customThe organic layer is separated
  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-cd3eb982504f451c9cdb4e6638c8c71d
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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