Potassium Hydroxide → Bis(4-ethynylphenyl)methanone

HRID 370299ノート

反応式

HRID 370299 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 3112529Bis(4-ethynylphenyl)methanone収率 68%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-c8b7aa3a30f144b0bf6c7a464755157b
出典データセット
uspto-grants-2000_10
特許番号
US06140503

反応ノート

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