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

HRID 2369631ノート

反応式

HRID 2369631 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 241Benzene溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-a0ff9380560945bba129be135c49328e
出典データセット
uspto-grants-2014_04
特許番号
US08703978B2

反応ノート

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