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

HRID 1823634

反応式

HRID 1823634 の反応式
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]

参加物

7

反応物 4

HCID 962Water2 回HCID 10340Sodium CarbonateHCID 27733952,3-Dimethylphenylboronic acidHCID 117898227-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 174Ethylene Glycol溶媒

反応条件

温度
125 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-45ac6cb26d6941bab379c4760ec65189
出典データセット
uspto-grants-2006_05
特許番号
US07038070B2

関連ノート

読み込み中…