Potassium Hydroxide → 2-Methyl-1-phenyl-pyrrole

HRID 880455

반응식

HRID 880455 반응식
[C:1]1([N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[CH:12]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].O.NN>C(O)CO>[CH3:12][C:8]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 9347291-phenyl-1H-pyrrole-2-carbaldehyde

생성물 1

HCID 46530262-Methyl-1-phenyl-pyrrole수율 66.7%

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

실험 절차

A mixture of 1-phenylpyrrole-2-carbaldehyde (700 mg, 4.1 mmol), potassium hydroxide (490 mg, 12.3 mmol) and hydrazine hydrate (0.8 mL, 12.3 mmol) in ethylene glycol (15 mL) was stirred at ambient temperature for 30 min and then slowly heated to 150° C. and maintained for 2 h. The reaction mixture was allowed to cool to ambient temperature, poured into ice-water and extracted with diethyl ether. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude compound. Purification by column chromatography over silica gel (60-120 mesh) using petroleum ether as eluent to afford 2-methyl-1-phenyl-pyrrole (430 mg, 66%) as a yellow oil.

후처리

  1. temperatureslowly heated to 150° C.
  2. temperaturemaintained for 2 h
  3. temperatureto cool to ambient temperature
  4. extractionextracted with diethyl ether
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude compound
  10. customPurification by column chromatography over silica gel (60-120 mesh)

출처 및 근거

ORD 기록
ord-9e7277e56ab44dc1aff4ee6223583bf7
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993574B2

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