Reaktion #1558926

Reaktionsgleichung

Ethylmagnesium bromide

3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)picolinonitrile

THF

→

1-(3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)propan-1-one

Ausbeute 58.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition
2. 2
   Sonstigequenched with aqueous citric acid solution
3. 3
   ExtraktionThe aqueous layer was extracted with EtOAc (2×30 mL)
4. 4
   WaschenThe combined organic layers were washed with NaHCO3(sat) solution and brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated
7. 7
   Sonstigepurified on silica gel using
8. 8
   workup.ADDITIONa mixture of EtOAc and hexanes as eluent

Vorschrift

Ethylmagnesium bromide (3M/ether, 1.53 mL, 4.60 mmol, 1.5 eq.) was added to a stirred solution of 3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)picolinonitrile (960 mg, 3.07 mmol, 1 eq.) in THF (15.0 mL) at −78° C. After addition, the reaction mixture was allowed to warm to rt and quenched with aqueous citric acid solution. The aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were washed with NaHCO3(sat) solution and brine, dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 1-(3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)propan-1-one (611 mg, 58%) as a colorless oil. LRMS (M+H+) m/z 345.1.

Quelle