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

HRID 127161

反応式

HRID 127161 の反応式
[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]

参加物

3

反応物 2

HCID 103992Methyl 1-methylpyrrol-2-acetate2 回HCID 641326Oxo-P-tolyl-acetonitrile

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6485920042fe41719bbc666e5ea2aa49
出典データセット
uspto-grants-1981_03
特許番号
US04255335

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