Reaktion #2161290

Reaktionsgleichung

1-trityl-1H-imidazole-4-carbaldehyde

methyl magnesium bromide

→

title compound

Ausbeute 75.2%

1-(1-trityl-1H-imidazol-4-yl)ethanol

Ausbeute 75.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   SonstigeThe reaction was quenched with sat. aq. NH4Cl (50 mL)
3. 3
   Extraktionthe mixture extracted with CH2Cl2 (3×50 mL)
4. 4
   Waschenwashed with 1 N aq. NaOH (3×20 mL), water (3×20 mL) and brine (100 mL)
5. 5
   Trocknendried over MgSO4
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified via column chromatography (silica gel, EtOAc/Petroleum ether 1:5)

Vorschrift

To a solution of 1-trityl-1H-imidazole-4-carbaldehyde (10.0 g, 0.03 mol) in anhydrous THF (100 mL) was added dropwise methyl magnesium bromide (1.4 M in hexane, 52.8 mL, 0.075 mol) at 0° C. After the addition, the mixture was stirred at RT overnight. The reaction was quenched with sat. aq. NH4Cl (50 mL) and the mixture extracted with CH2Cl2 (3×50 mL). The organic layers were combined, washed with 1 N aq. NaOH (3×20 mL), water (3×20 mL) and brine (100 mL), dried over MgSO4 and evaporated. The residue was purified via column chromatography (silica gel, EtOAc/Petroleum ether 1:5) to yield the title compound (8.0 g, 75.0%) as a white solid.

Quelle