반응 #614903

반응 방정식

4-methyl-3-(methyloxy)phenol

potassium carbonate

2-chloro-5-nitropyridine

→

title compound

수율 75.7%

2-{[4-methyl-3-(methyloxy)phenyl]oxy}-5-nitropyridine

수율 75.7%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   기타The reaction was quenched with water (10 mL)
2. 2
   workup.ADDITIONdiluted with brine (20 mL)
3. 3
   추출extracted with ethyl acetate (3 times 30 mL)
4. 4
   세척The organic layer was washed with ice cold brine (2 times 30 mL)
5. 5
   건조dried over sodium sulphate
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타The residue was purified by silica gel chromatography (Biotage system, 100 g SNAP column) with a gradient cyclohexane/ethyl acetate from 10/0 to 8/2
9. 9
   기타Evaporation

실험 절차

To a solution of 4-methyl-3-(methyloxy)phenol (Reference Intermediate R2, 400 mg) in dry N,N-dimethylformamide (15 mL), potassium carbonate (1200 mg, 8.69 mmol) and then 2-chloro-5-nitropyridine (551 mg, 3.47 mmol) were added and the reaction mixture was stirred for 2 hours at 115° C. The reaction was quenched with water (10 mL), diluted with brine (20 mL) and extracted with ethyl acetate (3 times 30 mL). The organic layer was washed with ice cold brine (2 times 30 mL), dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography (Biotage system, 100 g SNAP column) with a gradient cyclohexane/ethyl acetate from 10/0 to 8/2. Evaporation afforded the to title compound as a light yellow oil (570 mg).

출처