Trimethylsilylacetylene → 1-Ethynyl-4-pentylbenzene

HRID 1613527ノート

反応式

HRID 1613527 の反応式
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9](I)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C[Si]([C:17]#[CH:18])(C)C>C(NCC)C.[Cu]I>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:17]#[CH:18])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

参加物

5

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 1450574-Iodopentylbenzene

生成物 1

HCID 27751311-Ethynyl-4-pentylbenzene

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8021Diethylamine溶媒

実験手順

A mixture of 0.1 mol of 4-pentyliodobenzene, 0.12 mol of trimetylsilylacetylene, 0.0014 mol of bis(triphenylphosphine)-palladium(II) Chloride Pd(PPh3)2Cl2 and 0.7 mmol of copper (I) iodide in 250 ml diethylamine is stirred at room temperature for 20 hours. After evaporation of the solvent the crude product is purified by chromatography on alumina (4:1 petrol/dichloromethane) to give 2-(4-pentylphenyl)-1-trimethylsilyacetylene. Removal of the trimethylsilylgroup is accomplished by treatment this acetylene is methanol with 1 M KOH for 1 hour at room temperature. Evaporation of the methanol and either extraction yields 4-pentylphenylacetylene.

後処理

  1. customAfter evaporation of the solvent the crude product
  2. customis purified by chromatography on alumina (4:1 petrol/dichloromethane)
  3. customto give 2-(4-pentylphenyl)-1-trimethylsilyacetylene
  4. customRemoval of the trimethylsilylgroup
  5. customfor 1 hour
  6. customat room temperature
  7. customEvaporation of the methanol
  8. extractioneither extraction

出典と根拠

ORDレコード
ord-8d3750c7882344f3845bdb3d1508da83
出典データセット
uspto-grants-1993_03
特許番号
US05194178

反応ノート

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