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Sodium Carbonate → 7-(3,5-Dimethylphenyl)-2-methyl-1-indanone

HRID 2298472
ノート
印刷プレビュー

反応式

HRID 2298472 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[CH:15]=[C:16](B(O)O)[CH:17]=[C:18]([CH3:20])[CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC1C=CC=CC=1C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:13][C:14]1[CH:15]=[C:16]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:10]=2[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]3)[CH:17]=[C:18]([CH3:20])[CH:19]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343493,5-Dimethylphenylboronic acidHCID 117898227-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one

生成物 1

HCID 221731007-(3,5-Dimethylphenyl)-2-methyl-1-indanone収率 90.1%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
2 回
HCID 962Water溶媒2 回
HCID 7237O-Xylene溶媒

反応条件

温度
100 °C

実験手順

Using a method similar to Example 16b), 16.25 g (0.09 mol) of (1), 14.85 g (0.1 mol) of 3,5-dimethylphenylboronic acid, 21.2 g (0.2 mol) of sodium carbonate were placed in 240 ml of o-xylene/80 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 101 mg (0.45 mmol) of palladium acetate and 472 mg (1.8 mmol) of TPP, the reaction mixture was stirred for 8 hours at 100° C. After 2, 4 and 6 hours, the same amounts of palladium acetate and triphenylphosphine were added again each time. After addition of 150 ml of water, the phases were separated, the aqueous phase was extracted 3 times with 200 ml each time of ether, the combined organic phases were washed with 200 ml of water and 200 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 20.3 g of (17) as an oil.

後処理

  1. customthe mixture was degassed a number of times
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted 3 times with 200 ml each time of ether
  4. washthe combined organic phases were washed with 200 ml of water and 200 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-e5abbbd49fa2470ea59afe5317c7a7b9
出典データセット
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06492539B1

反応ノート

読み込み中…

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