Reaktion #2192207

Reaktionsgleichung

Intermediate 188.3

3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorobenzaldehyde

Intermediate 217.1

4-(2-bromophenyl)-1-trityl-1H-imidazole

lithium diisopropylamide

→

Intermediate 217.2

Ausbeute 54.1%

(4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)methanol

Ausbeute 54.1%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at 0° C. for 2 h
2. 2
   Sonstigewas quenched with sat. NH4Cl
3. 3
   workup.ADDITIONdiluted with EtOAc
4. 4
   WaschenThe organic phase was washed with H2O and brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient)

Vorschrift

To a solution of Intermediate 217.1 (650 mg, 1.40 mmol) in 10 mL THF at 0° C., was added a solution of lithium diisopropylamide (2M in heptane/THF/ethylbenzene, 0838 mL, 1.68 mmol). The mixture was stirred at 0° C. for 30 min, then a solution of Intermediate 188.3 (356 mg, 1.26 mmol) in 2 mL THF. The mixture was stirred at 0° C. for 2 h, then was quenched with sat. NH4Cl and diluted with EtOAc. The organic phase was 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 510 mg of Intermediate 217.2 as a pale yellow solid. LCMS (50 to 100% B, 4 min gradient, A=95% H2O/5% CH3CN/0.1% TFA, B=5% H2O/95% CH3CN/0.1% TFA) RT=5.61 min, 747.67 (M+H)+.

Quelle