反応 #46778

反応方程式

3-bromo-1,1,1-trifluoropropan-2-one oxime

indole

indole

sodium carbonate

→

1,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-one oxime

収率 89.2%

溶媒

methyl tert-butyl ether

反応条件

後処理

1. 1
   その他to afford a new more polar product
2. 2
   ろ過The mixture was then filtered through diatomaceous earth
3. 3
   濃縮concentrated in vacuo
4. 4
   濃縮The residue was then concentrated in vacuo
5. 5
   workup.ADDITIONdiluted first with dichloromethane (1 part)

実験手順

To a solution of the 1.64 g (7.96 mmol) of 3-bromo-1,1,1-trifluoropropan-2-one oxime in 250 mL of methyl tert-butyl ether was added 3.74 g (31.92 mmol) of indole followed by 5.0 g (47.62 mmol) of powdered (freshly ground) sodium carbonate. The reaction was monitored by thin layer chromatography (ethyl acetate-hexanes (2:8)) to afford a new more polar product compared to indole (PMA-stained and UV-active). The mixture was then filtered through diatomaceous earth and concentrated in vacuo. The residue was then concentrated in vacuo and diluted first with dichloromethane (1 part) and then hexanes (4 parts) and passed through a pad of silica gel using dichloromethane-hexanes (gradient: 20%-100%) to afford 1.72 g (89.2%) of 1,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-one oxime as a white solid.

出典