4-phenyl-1-(triphenylmethyl)-1H-imidazole → (5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-phenyl-1-trityl-1H-imidazol-2-yl)methanol

HRID 2104962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2104962
[C:1]1([C:7]2[N:8]=[CH:9][N:10]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[CH2:36]([O:38][C:39]1[CH:40]=[C:41]([O:48][CH:49]([CH3:51])[CH3:50])[C:42]([F:47])=[C:43]([CH:46]=1)[CH:44]=[O:45])[CH3:37]>C1COCC1>[CH2:36]([O:38][C:39]1[CH:40]=[C:41]([O:48][CH:49]([CH3:50])[CH3:51])[C:42]([F:47])=[C:43]([CH:44]([C:9]2[N:10]([C:12]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:11]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[OH:45])[CH:46]=1)[CH3:37]

Komponenten

5

Edukt 3

HCID 102217694-phenyl-1-(triphenylmethyl)-1H-imidazoleHCID 862472095-Ethoxy-2-fluoro-3-isopropoxybenzaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 68813196(5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-phenyl-1-trityl-1H-imidazol-2-yl)methanolAusbeute 75,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of Intermediate 8.1 (200 mg, 0.517 mmol) in 3 mL THF at 0° C., was added BuLi (1.4 M in THF, 0.406 mL, 0.569 mmol). The mixture was stirred at 0° C. for 25 min, then a solution of Intermediate 7.2 (117 mg, 0.517 mmol) in 1 mL THF was added dropwise. The mixture was stirred at 0° C. for 30 min, then was quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient) to afford 240 mg of Intermediate 25.1 as a colorless solid.

Aufarbeitung

  1. stirringThe mixture was stirred at 0° C. for 30 min
  2. customwas quenched with sat. NH4Cl
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-82c678c85dfc489099ebd5eff43e4600
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576098B2

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