Reaktion #1558905

Reaktionsgleichung

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

HCl

→

5-((2-(2-hydroxypropan-2-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde

Ausbeute 99.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturO/N, cooled to rt
2. 2
   Extraktionextracted with EtOAc twice
3. 3
   WaschenThe combined organic layers were washed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated
6. 6
   Sonstigepurified on silica gel using
7. 7
   workup.ADDITIONa mixture of EtOAc and hexanes as eluent

Vorschrift

To 2-(3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)propan-2-ol (30 mg, 0.087 mmol, 1 eq.) in a RB flask was added HCl (6 N, 3.0 mL). The mixture was warmed to 40° C., O/N, cooled to rt, neutralized to pH 7-8 with NaHCO3(sat) solution, and extracted with EtOAc twice. The combined organic layers were washed with brine, dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 5-((2-(2-hydroxypropan-2-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (10.2 mg, 99%) as a pale-yellow oil. 1H NMR (400 MHz, CDCl3) δ 10.36 (s, 1H), 8.46 (dd, J=4.7, 1.6 Hz, 1H), 7.99 (s, 1H), 7.86 (dd, J=7.8, 1.5 Hz, 1H), 7.24 (dd, J=7.8, 4.7 Hz, 1H), 7.05 (s, 1H), 5.37 (s, 2H), 3.85 (s, 3H), 1.57 (s, 6H). LRMS (M+H+) m/z 303.1.

Quelle