1,2-Dimethoxyethane → 5-(2-methylphenyl)-1H-pyrrole-3-carbaldehyde

HRID 1012463

反応式

HRID 1012463 の反応式
Br[C:2]1[NH:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1.[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>O>[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:2]1[NH:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1

参加物

6

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 578319835-bromo-1H-pyrrole-3-carbaldehyde

生成物 1

HCID 862327865-(2-methylphenyl)-1H-pyrrole-3-carbaldehyde収率 68%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
105 °C

実験手順

5-Bromo-1H-pyrrole-3-carbaldehyde (100 mg), 2-methylphenylboronic acid (94 mg) and sodium carbonate (146 mg) were suspended in a mixed solvent of 1,2-dimethoxyethane (5 mL) and water (2 mL), and the mixture was sufficiently degassed under a nitrogen atmosphere. Tetrakis(triphenylphosphine)palladium (33 mg) was added, and the mixture was further degassed and refluxed at 105° C. for 24 hr. The reaction mixture was allowed to cool to room temperature, and the mixture was extracted with water and ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=8:1→3:1) to give the title compound as colorless crystals (yield 72 mg, 68%).

後処理

  1. customthe mixture was sufficiently degassed under a nitrogen atmosphere
  2. additionTetrakis(triphenylphosphine)palladium (33 mg) was added
  3. customthe mixture was further degassed
  4. temperatureto cool to room temperature
  5. extractionthe mixture was extracted with water and ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=8:1→3:1)

出典と根拠

ORDレコード
ord-8fbad435454c498e9f2d344942adc1d1
出典データセット
uspto-grants-2011_07
特許番号
US07977488B2

関連ノート

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