Trimethylsilylacetylene → 1-Ethynyl-4-pentylbenzene

HRID 1613527노트

반응식

HRID 1613527 반응식
[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]

참가 물질

5

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 1450574-Iodopentylbenzene

생성물 1

HCID 27751311-Ethynyl-4-pentylbenzene

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8021Diethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8d3750c7882344f3845bdb3d1508da83
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05194178

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