Hexane → Methyl 4-[2-(1,1-dimethyl-3-oxo-indan-5-yl)vinyl]benzoate

HRID 53285

반응식

HRID 53285 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=[CH2:15].C(=O)(O)[O-].[Na+].CCCCCC>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O.C(Cl)Cl>[CH3:12][C:6]1([CH3:13])[C:5]2[C:9](=[CH:10][C:2]([CH:15]=[CH:14][C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=3)=[CH:3][CH:4]=2)[C:8](=[O:11])[CH2:7]1

참가 물질

11

반응물 4

HCID 8058HexaneHCID 516892Sodium BicarbonateHCID 583124Methyl 4-ethenylbenzoateHCID 107763656-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 54336622Methyl 4-[2-(1,1-dimethyl-3-oxo-indan-5-yl)vinyl]benzoate수율 70%

시약·촉매·용매 6

HCID 167845palladium(II) acetate촉매HCID 16212273Tetrabutylammonium chloride hydrate촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

6-Bromo-3,3-dimethyl-indan-1-one (1.20 g, 5.02 mmol), methyl 4-vinylbenzoate (1.63 g, 10.0 mmol), palladium acetate (56 mg, 0.25 mmol), tetrabutylammonium chloride hydrate (1.53 g, 5.52 mmol ), and sodium bicarbonate (1.05 g, 12.6 mmol) were stirred in 10 mL of anhydrous N,N-dimethylformamide at 80°-100° C. for 8 hours. The mixture was diluted with water (100 mL), extracted with methylene chloride (50 mL×3). The combined extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (CH2Cl2 :hexane=1:1 to 1:0, then CH2Cl2 :EtOAc=10:1) to give 1.12 g (70% yield) of the title compound as a yellow solid; 1H-NMR (CDCl3) δ1.45 (s, 6H), 2.64 (s, 2H), 5.30 (s, 3H), 7.18 (d, J=16.5 Hz, 1H), 7.26 (d, J=16.5 Hz, 1H), 7.52 (d, J=8.1 Hz, 1H), 7.58 (d, J=8.5 Hz, 2H), 7.78 (d, J=1.7, 8.1 Hz, 1H), 7.86 (d, J=1.7 Hz, 1H), 8.05 (d, J=8.5 Hz, 2H); MS m/e 321 (MH+).

후처리

  1. extractionextracted with methylene chloride (50 mL×3)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by flash chromatography (CH2Cl2

출처 및 근거

ORD 기록
ord-e894fad907b74d91b47cdd45f501a1db
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618839

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