Acetone → 1-(3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinolin-4-yl)-but-1-en-3-one

HRID 2118853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118853
[Cl:1][C:2]1[N:3]=[C:4]([CH3:14])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH:12]=O.[OH-].[Na+].O.[CH3:18][C:19]([CH3:21])=[O:20]>>[Cl:1][C:2]1[N:3]=[C:4]([CH3:14])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:11]=1[CH:12]=[CH:18][C:19](=[O:20])[CH3:21]

Komponenten

5

Edukt 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 139353363-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carboxaldehyde

Produkt 1

HCID 537568801-(3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinolin-4-yl)-but-1-en-3-one

Versuchsvorschrift

3-Chloro-1-methyl-5,6,7,8-tetrahydroisoquinoline-4-carboxaldehyde (4.0 g) was stirred with a few drops of a 2% aqueous sodium hydroxide solution in aqueous acetone (1:2 v/v; 20 ml) at room temperature for 4 hr. the mixture was poured into water which was then extracted with the diethyl ether. The residue obtained after evaporation of the dried (MgSO4) organic extract was purified by column chromatography over silica with dichloromethane elution to give 1-(3-chloro-1-methyl-5,6,7,8-tetrahydroisoquinolin-4-yl)-but-1-en-3-one as white crystals, mp 90° C.

Aufarbeitung

  1. extractionwas then extracted with the diethyl ether
  2. customThe residue obtained
  3. customafter evaporation of the
  4. dry with materialdried (MgSO4)
  5. extractionorganic extract
  6. customwas purified by column chromatography over silica with dichloromethane elution

Quellen und Nachweise

ORD-Eintrag
ord-ab9f6f05c203449c8d039107e6e16a03
Quelldatensatz
uspto-grants-1987_07
Patentnummer
US04680400

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