Methyl 1-methylpyrrol-2-acetate → Methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate

HRID 127161

반응식

HRID 127161 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](C#N)=[O:7])=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][C:19]([O:21][CH3:22])=[O:20]>>[CH3:12][N:13]1[C:17]([C:6](=[O:7])[C:5]2[CH:10]=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:16][CH:15]=[C:14]1[CH2:18][C:19]([O:21][CH3:22])=[O:20]

참가 물질

3

반응물 2

HCID 103992Methyl 1-methylpyrrol-2-acetate2회HCID 641326Oxo-P-tolyl-acetonitrile

생성물 1

HCID 118468Methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate수율 398.8%

실험 절차

A mixture of 5.0 g (0.034 mole) of 4-methylbenzoylcyanide and 0.8 g (0.005 mole) of methyl 1-methyl-pyrrole-2-acetate was added over 4 hours from a heated addition funnel to a sample of 3.8 g (0.025 mole) of methyl 1-methylpyrrole-2-acetate at 180° through which nitrogen was bubbled. The mixture was heated for six more hours after the addition was complete. The reaction was cooled and dissolved in methylene chloride-toluene. The organic solution was washed with 10 percent sodium hydroxide solution and saturated brine and dried (MgSO4). The solvent was evaporated in vacuo and the residue recrystallized twice from methanol to give 5.41 g (69 percent yield) of white crystalline methyl 1-methyl-5-(4-methyl-benzoyl)-pyrrole-2-acetate, mp 118°-120° C. The solid state IR spectrum was identical to authentic material.

후처리

  1. customwas bubbled
  2. temperatureThe mixture was heated for six more hours
  3. additionafter the addition
  4. temperatureThe reaction was cooled
  5. dissolutiondissolved in methylene chloride-toluene
  6. washThe organic solution was washed with 10 percent sodium hydroxide solution and saturated brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated in vacuo
  9. customthe residue recrystallized twice from methanol

출처 및 근거

ORD 기록
ord-6485920042fe41719bbc666e5ea2aa49
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04255335

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