Water → 2,4,7,9-Tetraphenyl-1,10-phenanthroline

HRID 1367800ノート

反応式

HRID 1367800 の反応式
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:27]=[CH:26][N:25]=[C:24]3[C:15]=2[CH:16]=[CH:17][C:18]2[C:23]3=[N:22][CH:21]=[CH:20][C:19]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:10][CH:9]=1.O>C1(C)C=CC=CC=1.C1COCC1>[C:1]1([C:21]2[CH:20]=[C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:18]3[C:23](=[C:24]4[C:15](=[CH:16][CH:17]=3)[C:14]([C:11]3[CH:10]=[CH:9][CH:8]=[CH:13][CH:12]=3)=[CH:27][C:26]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:25]4)[N:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 962WaterHCID 728124,7-Diphenyl-1,10-phenanthrolineHCID 178506676HCID 178506676、化合物

生成物 1

HCID 155677992,4,7,9-Tetraphenyl-1,10-phenanthroline収率 90%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Under a nitrogen atmosphere, 15 ml of a 1.6 mol/l phenyllithium solution (24 mmole) was added to a stirred suspension of 2.0 g of bathophenanthroline (6 mmole) in a mixture of 60 ml of toluene and 20 ml of THF, and the resulting mixture was cooled to 0° C. The resulting deep-red solution was stirred overnight at room temperature, and 10 ml of water was then added. The organic layer was separated, and the aqueous layer was extracted with 40 ml of dicholormethane three times. The combined extracts were stirred with 30 g of MnO2 for 2 hours. The mixture was dried over 30 g of anhydrous MgSO4, filtered, and evaporated to give 2.6 g of a light yellow solid in a yield of 90 percent. 1H NMR (500 MHz, CDCl3), ppm: 8.50 (d, J=7.5 Hz, 4H), 8.09 (s, 2H), 7.81 (s, 2H), 7.61-7.57 (m, 8H), 7.55 (dd, J=7.5, 7.5 Hz, 4H), 7.52-7.47 (m, 4H). Analysis for PBP. Found: C, 88.62, H, 4.56, N, 5.82. Calculated: C, 89.23, H, 4.99, N, 5.78.

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with 40 ml of dicholormethane three times
  3. stirringThe combined extracts were stirred with 30 g of MnO2 for 2 hours
  4. dry with materialThe mixture was dried over 30 g of anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-835ec4afdb06440e87b0395da0c3a9cb
出典データセット
uspto-grants-2011_02
特許番号
US07893352B2

反応ノート

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