Imidazole → 1-Adamantyl 1-imidazolylmethyl ketone

HRID 259307

Reaktionsgleichung

Reaktionsgleichung von HRID 259307
Br[CH2:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4].CN(C)C=O.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1>O>[NH:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 6228Dimethylformamide2×HCID 197820Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketone

Produkt 1

HCID 433411781-Adamantyl 1-imidazolylmethyl ketone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 5 g. of 1-adamantyl bromomethyl ketone in 10 ml. of dimethylformamide is added dropwise with stirring and ice-cooling to 7 g. imidazole in 10 ml. dimethylformamide. The resulting solution is stirred overnight at room temperature and then poured into 250 ml. water. The precipitate which forms is filtered off, washed with water and air dried. Thereafter the resulting residue is chromatographed on silica gel to effect purification. Elution with 10% acetone in dichloromethane yields 1-adamantyl 1-imidazolylmethyl ketone, M.P. 128.5°-129.5° C.

Aufarbeitung

  1. temperatureice-cooling to 7 g
  2. stirringThe resulting solution is stirred overnight at room temperature
  3. additionpoured into 250 ml
  4. filtrationThe precipitate which forms is filtered off
  5. washwashed with water and air
  6. customdried
  7. customThereafter the resulting residue is chromatographed on silica gel
  8. custompurification
  9. washElution with 10% acetone in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b47529ff2e8c445b9a39986abbb92714
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04036975

Verknüpfte Notizen

Wird geladen…