반응 #165431

반응 방정식

4-hydroxybenzaldehyde

2-fluoropyridine

sodium hydride

→

title compound

수율 57.0%

4-(Pyridin-2-yloxy)-benzaldehyde

수율 57.0%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.WAITfor 45 minutes at 140° C.
2. 2
   workup.WAITfor 2 hours at 160° C
3. 3
   온도The mixture was cooled to room temperature
4. 4
   기타partitioned into ethyl acetate and water
5. 5
   기타The organic layer was separated
6. 6
   세척washed with water (three times)
7. 7
   여과filtered
8. 8
   농축The filtrate was concentrated under a reduced pressure
9. 9
   기타the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1)

실험 절차

To an N,N-dimethylformamide solution (100 mL) of 4-hydroxybenzaldehyde (10 g, 82 mmol) and 2-fluoropyridine (8.0 g, 82 mmol) was added sodium hydride (3.3 g, 82 mmol, 60% in oil), which was stirred for 30 minutes at 120° C., then for 45 minutes at 140° C., and then for 2 hours at 160° C. The mixture was cooled to room temperature and partitioned into ethyl acetate and water. The organic layer was separated, washed with water (three times), and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1) to obtain the title compound (9.3 g, 57%).

출처