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

HRID 254133

반응식

HRID 254133 반응식
[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

참가 물질

6

반응물 4

HCID 887MethanolHCID 695049-AnthracenecarboxaldehydeHCID 699119-AcetylanthraceneHCID 178418582HCID 178418582, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  1. filtrationthe precipitate was filtered off
  2. customvacuum dried

출처 및 근거

ORD 기록
ord-58ba6851f1c1459fa1ee1ffadca931cb
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875408B2

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