Methanol → 1,3-Di(anthracene-9-yl)-2-propene-1-one

HRID 254133

反応式

HRID 254133 の反応式
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH:15]=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[C:17]([C:20]1[C:21]2[C:26]([CH:27]=[C:28]3[C:33]=1[CH:32]=[CH:31][CH:30]=[CH:29]3)=[CH:25][CH:24]=[CH:23][CH:22]=2)(=O)[CH3:18].CO[Na].CO>CN(C=O)C>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[C:15](=[O:16])[CH:18]=[CH:17][C:20]2[C:33]4[C:28]([CH:27]=[C:26]5[C:21]=2[CH:22]=[CH:23][CH:24]=[CH:25]5)=[CH:29][CH:30]=[CH:31][CH:32]=4)=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

参加物

6

反応物 4

HCID 887MethanolHCID 695049-AnthracenecarboxaldehydeHCID 699119-AcetylanthraceneHCID 178418582HCID 178418582、化合物

生成物 1

HCID 860332911,3-Di(anthracene-9-yl)-2-propene-1-one収率 91.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

9-anthraldehyde (10 mmol, 2.06 g) and 9-acetylanthracene (10 mmol, 2.2 g) were combined in dry DMF under N2 and MeONa (28 mmol, 1.5 g) was added. The reaction mixture is stirred overnight. Then MeOH was added (60 mL) and the precipitate was filtered off and vacuum dried to afford 3.73 g of pure 1,3-di(anthracene-9-yl)-2-propene-1-one. Portion of it (2.5 mmol, 1 g) was suspended in a mixture of dioxane and MeOH (60 mL and 20 mL respectively) and heated to 75° C. at which point sodium borohydride (5.3 mmol, 200 mg) was added. The mixture was stirred for 5 min and 50 mL of water was added. After the mixture had cooled to ambient, the solids were filtered off, washed with water and vacuum dried affording 620 mg of the title product.

後処理

  1. filtrationthe precipitate was filtered off
  2. customvacuum dried

出典と根拠

ORDレコード
ord-58ba6851f1c1459fa1ee1ffadca931cb
出典データセット
uspto-grants-2011_01
特許番号
US07875408B2

関連ノート

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