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

HRID 53285

反応式

HRID 53285 の反応式
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

参加物

11

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 6

HCID 167845palladium(II) acetate触媒HCID 16212273Tetrabutylammonium chloride hydrate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-e894fad907b74d91b47cdd45f501a1db
出典データセット
uspto-grants-1997_04
特許番号
US05618839

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