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

HRID 1585582노트

반응식

HRID 1585582 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-399443e6688741978447fe56e0ece08b
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05939417

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