Water → 2-Methyl-7-(2-thienyl)-1-indanone

HRID 1062927ノート

反応式

HRID 1062927 の反応式
Br[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.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1C1C=CC=CC=1P(C1C=CC=CC=1C1C=CC=CC=1C)C1C=CC=CC=1C1C=CC=CC=1C>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:14]3[S:13][CH:17]=[CH:16][CH:15]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 158697837-Bromo-2-methyl-2,3-dihydro-1H-inden-1-one

生成物 1

HCID 221731192-Methyl-7-(2-thienyl)-1-indanone収率 75.3%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 22172997Tris(o-tolylphenyl)phosphine触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

Using a method similar to Example 15 a), 11.25 g (0.05 mol) of (2), 13.4 g (0.055 mol) of thiophenylboronic acid and 11.7 g (0.11 mol) of sodium carbonate were placed in 190 ml of dimethoxyethane and 60 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 225 mg (1 mmol) of palladium acetate and 0.609 g (2 mmol) of tris(o-tolylphenyl)phosphine were added and the reaction mixture was stirred for 2 hours at 80° C. After addition of 150 ml of water, the mixture was extracted 4 times with 100 ml each time of diethyl ether, the ether phase was washed twice with 50 ml each time of water and dried over magnesium sulfate. Removal of the solvent gave 8.6 g of (22) as an oil.

後処理

  1. custom60 ml of water in the reaction vessel, the mixture was degassed a number of times
  2. extractionthe mixture was extracted 4 times with 100 ml each time of diethyl ether
  3. washthe ether phase was washed twice with 50 ml each time of water
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent

出典と根拠

ORDレコード
ord-e8491ed9cd7d4e51ac204772bbf58ce9
出典データセット
uspto-grants-2005_11
特許番号
US06963017B2

反応ノート

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