Reacción #973093

Ecuación de reacción

2-chloro-6-hydroxypyridine

2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

cesium carbonate

→

title compound

Rendimiento 94.0%

2-Chloro-6[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]pyridine

Rendimiento 94.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropartitioned between EtOAc (50 mL) and water (50 mL)
2. 2
   OtroThe organic fraction was separated
3. 3
   Lavadowashed with water (2×50 mL)
4. 4
   Secadobrine (50 mL), dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo

Procedimiento

To a stirred solution of 2-chloro-6-hydroxypyridine (0.58 g, 4.50 mmol) and 2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate (1.29 g, 4.50 mmol) in DMF (10 mL) was added cesium carbonate (2.97 g, 9.00 mmol). The reaction mixture was stirred at 85° C. for 18 h, and then partitioned between EtOAc (50 mL) and water (50 mL). The organic fraction was separated, washed with water (2×50 mL), then brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo to give the title compound (1.03 g, 94%) as an off-white solid that was used without further purification. δH (DMSO-d6) 7.78 (1H, dd, J 8.1 and 7.5 Hz), 7.11 (1H, dd, J 7.5 and 0.6 Hz), 6.86 (1H, dd, J 8.1 and 0.6 Hz), 4.45-4.35 (1H, m), 4.33-4.18 (2H, m), 4.11-4.01 (1H, m), 3.77 (1H, dd, J 8.5 and 6.2 Hz), 1.34 (3H, s), 1.29 (3H, s). LCMS (ES+) 244.1 (M+H)+, RT 3.63 minutes (Method 1).

Fuente