Hydrochloric Acid → Methyl [5-(4-methoxybenzoyl)-1-methyl-1H-pyrrol-2-yl]acetate

HRID 1282330ノート

反応式

HRID 1282330 の反応式
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:16][N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][C:23]([O:25][CH3:26])=[O:24].Cl>C(Cl)Cl>[C:1]([C:21]1[N:17]([CH3:16])[C:18]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:20]=1)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 103992Methyl 1-methylpyrrol-2-acetateHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 18424261Methyl [5-(4-methoxybenzoyl)-1-methyl-1H-pyrrol-2-yl]acetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 17.0 g. (0.1 mole) of p-anisoyl chloride and 13.3 g. (0.1 mole) of aluminum chloride in 200 ml. of methylene chloride is added over 5 minutes to a solution of methyl 1-methylpyrrole-2-acetate in 100 ml. of methylene chloride at ice bath temperature. The mixture is stirred for 25 minutes and poured into ice acidified with dilute hydrochloric acid. The organic layer is separated and the aqueous layer is washed with methylene chloride. The combined organic solutions are washed successively with dimethylaminopropylamine solution, dilute hydrochloric acid and brine and then dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuo to give a dark oily residue which is crystallized from 40 ml. of cold methanol. The solid is collected by filtration, washed with cold methanol and recrystallized from methanol to give white crystalline methyl 5-(p-anisoyl)-1-methylpyrrole-2-acetate, m.p. 104-105° C.

後処理

  1. additionpoured into ice
  2. customThe organic layer is separated
  3. washthe aqueous layer is washed with methylene chloride
  4. washThe combined organic solutions are washed successively with dimethylaminopropylamine solution, dilute hydrochloric acid and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent is evaporated in vacuo
  7. customto give a dark oily residue which
  8. customis crystallized from 40 ml
  9. filtrationThe solid is collected by filtration
  10. washwashed with cold methanol
  11. customrecrystallized from methanol

出典と根拠

ORDレコード
ord-60ba5e7191634211ac3a30ce3a27df56
出典データセット
uspto-grants-2002_09
特許番号
US06455703B2

反応ノート

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