반응 #2461350

반응 방정식

Methyl 3-hydroxycinchoninate

potassium carbonate

methyl iodide

→

methyl 3-methoxycinchoninate

용매

acetone

water

반응 조건

후처리

1. 1
   추출extracted into DCM
2. 2
   세척washed with satd
3. 3
   건조The organics were dried over Na2SO4
4. 4
   농축concentrated
5. 5
   기타Material purified by SGC (Combi flash, 10-50% EtOAc-hexanes over 40 minutes)

실험 절차

Methyl 3-hydroxycinchoninate, (J. Org. Chem. 1953, 18, 552) (1.53 g, 7.54 mmol), potassium carbonate (1.15 g, 8.29 mmol) in acetone (11 ml) was treated with methyl iodide (470 uL, 7.54 mmol) was stirred at RT under nitrogen overnight. The mixture diluted with water and extracted into DCM and washed with satd. sodium thiosulfate solution. The organics were dried over Na2SO4 and concentrated. Material purified by SGC (Combi flash, 10-50% EtOAc-hexanes over 40 minutes) gave methyl 3-methoxycinchoninate. 1H NMR (CDCl3) δ 8.85 (s, 1H), 8.07 (d, 1H), 7.72 (d, 1H), 7.61 (m, 2H), 4.08 (s, 3H), 4.03 (s, 1H). MS (ESI+) for m/z 218 (M+H)+.

출처