Ammonium Chloride → 1-benzyl-5-(4-(4-fluorophenyl)-1-hydroxybutyl]-1H-imidazole

HRID 744721

Reaktionsgleichung

Reaktionsgleichung von HRID 744721
[Mg].Br[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[CH2:13]([N:20]1[C:24]([CH:25]=[O:26])=[CH:23][N:22]=[CH:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:13]([N:20]1[C:24]([CH:25]([OH:26])[CH2:3][CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=2)=[CH:23][N:22]=[CH:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 27732391-Benzyl-1H-imidazole-5-carboxaldehydeHCID 5462224MagnesiumHCID 147371331-(3-Bromopropyl)-4-fluorobenzene

Produkt 1

HCID 194219941-benzyl-5-(4-(4-fluorophenyl)-1-hydroxybutyl]-1H-imidazoleAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

5,4 g of magnesium turnings are covered with 50 ml of dry tetrahydrofuran. A solution of 1-bromo-3-(4-fluorophenyl)propane (48,7 g) in 200 ml of dry tetrahydrofuran is then added dropwise to the mixture at such a rate that a smooth reaction is maintained. After the addition is complete, the reaction mixture is refluxed for one additional hour and cooled to room temperature. To the reaction mixture is then added dropwise the solution of 1-benzyl-5-imidazolecarbaldehyde (20,9 g) in 200 ml of tetrahydrofuran. After the addition is complete, the reaction mixture is refluxed for 2 hours, cooled and poured into cold saturated ammonium chloride solution. Tetrahydrofuran phase is removed and the water phase is extracted three times with ethyl acetate. Organic phases are combined, dried and evaporated to dryness. The residue is suspended with diethyl ether and filtered. Yield 86%.

Aufarbeitung

  1. customthat a smooth reaction
  2. temperatureis maintained
  3. additionAfter the addition
  4. temperaturethe reaction mixture is refluxed for one additional hour
  5. additionAfter the addition
  6. temperaturethe reaction mixture is refluxed for 2 hours
  7. temperaturecooled
  8. customTetrahydrofuran phase is removed
  9. extractionthe water phase is extracted three times with ethyl acetate
  10. customdried
  11. customevaporated to dryness
  12. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-ebc0367cb5794565b026ebd42a4a9b6f
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05559141

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