Reaktion #1558903

Reaktionsgleichung

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

SOCl2

MeOH

→

methyl 3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)picolinate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturto reflux O/N
3. 3
   Einengenconcentrated
4. 4
   ExtraktionThe aqueous layer was extracted with EtOAc three times
5. 5
   TrocknenThe combined organic layers were dried over Na2SO4
6. 6
   Einengenconcentrated
7. 7
   Sonstigepurified on silica gel using
8. 8
   workup.ADDITIONa mixture of EtOAc and hexanes as eluent

Vorschrift

To 3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)picolinic acid (55 mg, 0.17 mmol, 1 equiv) in MeOH (15 mL) was added SOCl2 (5.0 mL). The mixture was heated to reflux O/N, concentrated, and neutralized to pH 8-9 with NaHCO3(sat.) solution. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give methyl 3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)picolinate (51.5 mg, quantitative yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.44 (s, 1H), 8.67 (dd, J=4.6, 1.5 Hz, 1H), 8.14 (dd, J=8.0, 1.5 Hz, 1H), 8.03 (s, 1H), 7.51 (dd, J=8.0, 4.6 Hz, 1H), 7.06 (s, 1H), 5.60 (s, 2H), 3.95 (s, 3H), 3.85 (s, 3H). LRMS (M+H+) m/z 303.1.

Quelle