Reaktion #420989

Reaktionsgleichung

water

2-Chloro-4-iodopyridine

isopropylmagnesiumchloride lithium chloride

2-(2-chloro-5-methoxy-phenyl)-propionaldehyde

→

desired compound

2-(2-Chloro-5-methoxy-phenyl)-1-(2-chloro-pyridin-4-yl)-propan-1-ol

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled in an ice bath
2. 2
   workup.ADDITIONwas added drop wise over a period of 10 minutes
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   Waschenthe organic layer was washed with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane)

Vorschrift

2-Chloro-4-iodopyridine (1.03 g, CAS Reg. No. 153034-86-7) was dissolved in THF (50 mL) and a solution of isopropylmagnesiumchloride-lithium chloride complex (14% in THF, 3.13 mL) was added at RT over 3 minutes. The mixture was cooled in an ice bath and 2-(2-chloro-5-methoxy-phenyl)-propionaldehyde (710 mg) dissolved in THF (20 mL) was added drop wise over a period of 10 minutes. Stirring was continued for 1.5 hours. The reaction mixture was poured into water, extracted with ethyl acetate and the organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane) to give the desired compound as a yellow oil (734 mg). MS (m/e)=312.0 (MH+).

Quelle