Water → 2-Methyl-7-(2,3-dimethylphenyl)-1-indanone

HRID 1823634

반응식

HRID 1823634 반응식
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([CH3:20])[C:14]=3[CH3:13])[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

참가 물질

7

반응물 4

HCID 962Water2회HCID 10340Sodium CarbonateHCID 27733952,3-Dimethylphenylboronic acidHCID 117898227-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 221732842-Methyl-7-(2,3-dimethylphenyl)-1-indanone수율 105.3%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 174Ethylene Glycol용매

반응 조건

온도
125 °C

실험 절차

Using a method similar to Example 16 d), 2.0 g (0.011 mol) of (1), 1.95 g (0.013 mol) of 2,3-dimethylphenylboronic acid and 2.6 g (24.6 mmol) of sodium carbonate were placed in 55 ml of ethylene glycol/5 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 18 mg (0.09 mmol) of palladium acetate and 0.15 g (0.27 mmol) of TMSPP, the reaction mixture was stirred for 2 hours at 125° C. After addition of 60 ml of water, the aqueous phase was extracted 4 times with 60 ml each time of ether, the combined ether phases were washed with 60 ml of water and 60 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 2.9 g of 2-methyl-7-(2,3-dimethylphenyl)-1-indanone as solid.

후처리

  1. customsimilar to Example 16 d
  2. customthe mixture was degassed a number of times
  3. extractionthe aqueous phase was extracted 4 times with 60 ml each time of ether
  4. washthe combined ether phases were washed with 60 ml of water and 60 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-45ac6cb26d6941bab379c4760ec65189
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07038070B2

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