تفاعل #46778

معادلة التفاعل

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

المردود 89.2%

المذيبات

methyl tert-butyl ether

ظروف التفاعل

المعالجة

1. 1
   أخرىto afford a new more polar product
2. 2
   ترشيحThe mixture was then filtered through diatomaceous earth
3. 3
   تركيزconcentrated in vacuo
4. 4
   تركيزThe residue was then concentrated in vacuo
5. 5
   workup.ADDITIONdiluted first with dichloromethane (1 part)

الإجراء التجريبي

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.

المصدر