Reaktion #2192215

Reaktionsgleichung

Intermediate 228.2

5-Ethyl-2-fluoro-biphenyl

PMDTA

BuLi

Intermediate 175.1

4-bromo-1-trityl-1H-imidazole-2-carbaldehyde

→

Intermediate 228.3

Ausbeute 74.1%

(4-Bromo-1-trityl-1H-imidazol-2-yl)-(5-ethyl-2-fluoro-biphenyl-3-yl)-methanol

Ausbeute 74.1%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigerecooled to −78° C.
2. 2
   TemperaturThe mixture was warmed to rt over 0.5 h
3. 3
   SonstigeThe reaction was quenched with sat. NH4Cl
4. 4
   workup.ADDITIONwas diluted with EtOAc
5. 5
   WaschenThe organic phase was washed with H2O (2×) and brine
6. 6
   Trocknendried (Na2SO4)
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient)

Vorschrift

To a solution of Intermediate 228.2 (85 mg, 0.424 mmol) and PMDTA (0.10 mL, 0.478 mmol) in 4 ml THF at −78° C., was added BuLi (1.4 M in hexanes, 0.334 mL, 0.467 mmol). The mixture was stirred with warming to −40° C. over 30 min, recooled to −78° C., then a solution of Intermediate 175.1 (177 mg, 0.424 mmol) in 1.5 mL THF was added. The mixture was warmed to rt over 0.5 h. The reaction was quenched with sat. NH4Cl, then was diluted with EtOAc. The organic phase was washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient) to afford 194 mg of Intermediate 228.3 as a colorless solid.

Quelle