反応 #742278

反応方程式

(4-methoxyphenyl)hydrazine

3-methylbutan-2-one

→

5-methoxy-2,3,3-trimethyl-3H-indole

収率 45.4%

溶媒

HOAc

反応条件

後処理

1. 1
   濃縮The mixture was concentrated
2. 2
   workup.ADDITION1N NaOH was added until pH 9 to 10
3. 3
   抽出The aqueous solution was extracted with ethyl acetate (50 mL×3)
4. 4
   乾燥The combined organic layers were dried over Na2SO4
5. 5
   ろ過After filtration and concentration
6. 6
   その他the residue was purified by flash column chromatography

実験手順

A mixture of (4-methoxyphenyl)hydrazine (0.98 g, 7.1 mmol) and 3-methylbutan-2-one (1.53 g, 17.8 mmol) in 20 mL of HOAc was heated at 100° C. overnight. The mixture was concentrated and 1N NaOH was added until pH 9 to 10. The aqueous solution was extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by flash column chromatography to give 610 mg of 5-methoxy-2,3,3-trimethyl-3H-indole (45%). 1H NMR (CDCl3) δppm: 7.43 (dd, 1H), 6.81 (m, 2H), 3.83 (s, 3H), 2.26 (s, 3H), 1.28 (s, 6H). LC-MS (M+H): 190.16

出典