Sodium Carbonate → 4-Methyl-5-phenyl-1H-pyrrole-3-carbaldehyde

HRID 554312노트

반응식

HRID 554312 반응식
Br[C:2]1[N:6](S(C2C=CC=CC=2)(=O)=O)[CH:5]=[C:4]([CH:16]=[O:17])[C:3]=1[CH3:18].[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>COCCOC.O>[CH3:18][C:3]1[C:4]([CH:16]=[O:17])=[CH:5][NH:6][C:2]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 66827Phenylboronic AcidHCID 862327345-bromo-4-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

생성물 1

HCID 713628124-Methyl-5-phenyl-1H-pyrrole-3-carbaldehyde수율 81.1%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
100 °C

실험 절차

A suspension of 5-bromo-4-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (1.78 g), phenylboronic acid (1.37 g), dichloro[bis(triphenylphosphine)]palladium (0.19 g) and sodium carbonate (1.72 g) in 1,2-dimethoxyethane (30 mL)-water (10 mL) was stirred at 100° C. for 1 hr. 8 mol/L aqueous sodium hydroxide solution (15 mL) was added, and the mixture was stirred at 90° C. for 3 hr. After cooling, the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→1:1), and the obtained solid was washed with hexane to give the title compound as a pale-yellow solid (yield 815 mg, 69%).

후처리

  1. stirringthe mixture was stirred at 90° C. for 3 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→1:1)
  8. washthe obtained solid was washed with hexane

출처 및 근거

ORD 기록
ord-a74a70bfe43a4cb2931cf901d08132ae
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048909B2

반응 노트

불러오는 중…