Water → HCID 178450084, Verbindung

HRID 1368548

Reaktionsgleichung

Reaktionsgleichung von HRID 1368548
BrC1C=CC2C(=CC=C(OCF)C=2)C=1.[F:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([C:28]([C:33]1[N:34]=[CH:35][N:36](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:37]=1)([OH:32])[CH:29]([CH3:31])[CH3:30])[CH:22]=[CH:21]2.C([Li])CCC.C(C1N=CN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1)=O.O>CCOCC.CCCCCC.C1COCC1>[F:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([C:28]([C:33]1[N:34]=[CH:35][NH:36][CH:37]=1)([OH:32])[CH:29]([CH3:31])[CH3:30])[CH:22]=[CH:21]2

Komponenten

8

Edukt 4

HCID 962WaterHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 185202081-(6-Fluoromethyloxynaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol 2-Bromo-6-fluoromethyloxynaphthaleneHCID 178418339Butyllithium

Produkt 1

HCID 178450084HCID 178450084, VerbindungAusbeute 212,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

Production of 1-(6-Fluoromethyloxynaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol 2-Bromo-6-fluoromethyloxynaphthalene (2.10 g) was dissolved in ether (100 ml), and the solution was cooled to −70° C. To the solution was slowly added a solution of n-butyllithium in hexane (1.6 M, 5.7 ml), and the mixture was stirred at −70° C. for 20 min. To the mixture was added dropwise a solution of 4-formyl-1-trityl-1H-imidazole (1.58 g) in THF (10 ml). The mixture was stirred for 20 min at −70° C. To the mixture was added water, and the mixture was extracted with ethyl acetate and dried. The solvent was distilled off and the residue was purified by silica gel chromatography (eluent, hexane:ethyl acetate=1:1) followed by recrystallization from diisopropyl ether to give the titled compound (1.73 g) as colorless needles.

Aufarbeitung

  1. stirringThe mixture was stirred for 20 min at −70° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. customdried
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel chromatography (eluent, hexane:ethyl acetate=1:1)
  6. customfollowed by recrystallization from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3393665c27394134946795a64bd73413
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06573289B1

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