反応 #2028866

反応方程式

HCl

Ethyl trifluoroacetate

sodium methoxide

4′-chloroacetophenone

→

yellow-orange solid

収率 93.3%

4,4,4-trifluoro-1-[4-(chloro)phenyl]-butane-1,3-dione

収率 93.3%

溶媒

methyl tert-butyl ether

methyl tert-butyl ether

反応条件

後処理

1. 1
   workup.ADDITIONadded to the reaction dropwise over 5 minutes
2. 2
   workup.ADDITIONwas added
3. 3
   その他The organic layer was collected
4. 4
   洗浄washed with brine (75 mL)
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo

実験手順

Ethyl trifluoroacetate (23.52 g, 166 mmol) was placed in a 500 mL three-necked round bottom flask, and dissolved in methyl tert-butyl ether (75 mL). To the stirred solution was added 25% sodium methoxide (40 mL, 177 mmol) via an addition funnel over a 2 minute period. Next 4′-chloroacetophenone (23.21 g, 150 mmol) was dissolved in methyl tert-butyl ether (20 mL), and added to the reaction dropwise over 5 minutes. After stirring overnight (15.75 hours), 3N HCl (70 mL) was added. The organic layer was collected, washed with brine (75 mL), dried over MgSO4, filtered, and concentrated in vacuo to give a 35.09 g of yellow-orange solid. The solid was recrystallized from iso-octane to give 31.96 g (85%) of the dione: mp66°-67° C.

出典