Potassium Hydroxide → Bis(4-ethynylphenyl)methanone

HRID 370299노트

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HRID 370299 반응식
C[Si]([C:5]#[C:6][C:7]1[CH:26]=[CH:25][C:10]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][Si](C)(C)C)=[CH:15][CH:14]=2)=[O:12])=[CH:9][CH:8]=1)(C)C.[OH-].[K+]>CO>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:11]([C:10]2[CH:9]=[CH:8][C:7]([C:6]#[CH:5])=[CH:26][CH:25]=2)=[O:12])=[CH:14][CH:15]=1)#[CH:20]

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 10571474Bis(4-((trimethylsilyl)ethynyl)phenyl)methanone

생성물 1

HCID 3112529Bis(4-ethynylphenyl)methanone수율 68%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a flask containing a mixture of 4,4'-dibromobenzophenone (5.0 g, 14.7 mmol), PdCl2 (PPh3)2 (0.42 mg, 0.60 mmol), and CuI (60 mg, 0.30 mmol) was added THF (100 mL), iPr2NH (20 mL) and trimethylsilylacetylene (4.6 mL, 32.5 mmol) under a nitrogen atmosphere. The mixture was stirred at room temperature for 40 hours. The solvent was removed under vacuum, and the residue was extracted with CH2Cl2 /H2O. The organic layer was collected, dried over MgSO4, filtered through Al2O3, and pumped dry. The residue was recrystallized from CH2Cl2 /hexane at -30° C. to afford pale brown crystalline 4,4'-bis(trimethylsilylethynyl)benzophenone in 96% yield (5.29 g). 1H NMR (300 MHz, C6D6, 25° C., TMS): δ=0.25 (s, 18 H, CH3), 7.53 (d, J=8.6 Hz, 4 H, C6H4), 7.69 (d, 4 H, C6H4). To a mixture of 4,4'-bis(trimethylsilylethynyl)benzophenone (1.0 g, 2.67 mmol) and KOH (0.30 g, 5.36 mmol) was added 50 mL of MeOH and the solution was stirred at room temperature for 3 hours. The solution was then extracted with Et2O. The Et2O solution was pumped dry and the residue was chromatographed using EtOAc/hexane (1:50 to 1:5) as eluent to afford 4,4'-diethynylbenzophenone in 68% yield (0.42 g).

후처리

  1. extractionThe solution was then extracted with Et2O
  2. dry with materialThe Et2O solution was pumped dry
  3. customthe residue was chromatographed

출처 및 근거

ORD 기록
ord-c8b7aa3a30f144b0bf6c7a464755157b
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140503

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