Trimethylsilylacetylene → Benzenamine, N,N-dibutyl-4-[(trimethylsilyl)ethynyl]-

HRID 2369631Notes

Reaction equation

HRID 2369631 reaction equation
I[C:2]1[CH:16]=[CH:15][C:5]([N:6]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>CCN(CC)CC.C1C=CC=CC=1.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>[CH3:17][Si:18]([C:21]#[C:22][C:2]1[CH:16]=[CH:15][C:5]([N:6]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH2:9][CH3:10])=[CH:4][CH:3]=1)([CH3:20])[CH3:19]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 13169159N,N-Dibutyl-4-iodoaniline

Product 1

HCID 12079525Benzenamine, N,N-dibutyl-4-[(trimethylsilyl)ethynyl]-Yield 82.2%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 241BenzeneSolventHCID 8471TriethylamineSolvent

Procedure

Cuprous iodide (23 mg, 1 mol %) was added to 4-iodo-N,N-dibutylaniline (4 g, 12.1 mmol), trimethylsilylacetylene (2.37 g, 24.2 mmol) and Pd(PPh3)2Cl2 (84 mg, 1 mol %) in dry Et3N (40 mL) under nitrogen. The resulting solution was stirred at room temperature for 16 h, diluted with benzene (50 mL), filtered and the solvent removed under reduced pressure. The residue was chromatographed on alumina using benzene as eluent. The solvent was removed under reduced pressure to give the title compound (3.0 g, 82%) as a pale yellow oil.

Workup

  1. filtrationfiltered
  2. customthe solvent removed under reduced pressure
  3. customThe residue was chromatographed on alumina
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a0ff9380560945bba129be135c49328e
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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