反応 #40648

反応方程式

phosphonium bromide

[2-(4-Fluorophenyl)ethyl]triphenylphosphonium bromide

benzyl 4-oxo-1-piperidinecarboxylate

water

→

title compound

収率 17.2%

4-[2-(4-Fluorophenyl)ethylidene]-piperidine-1-carboxylic acid benzyl ester

収率 17.2%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added at 0° C.
2. 2
   その他giving a deep red solution
3. 3
   workup.STIRRINGThe mixture was stirred at rt for 20 h
4. 4
   抽出the mixture extracted three times with diethylether
5. 5
   乾燥The combined organic layers were dried over Na2SO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo
8. 8
   その他Purification of the residue by silica gel column chromatography
9. 9
   洗浄eluting with a stepwise gradient of 0-10% ethyl acetate in n-heptane

実験手順

To a suspension of phosphonium bromide 78NLS66 (4.69 g, 10.1 mmol) in THF (100 mL) n-butyllithium (1.6 M in hexane, 6.3 mL, 10.1 mmol) was added at 0° C., giving a deep red solution. After stirring for 1 h at rt, a solution of benzyl 4-oxo-1-piperidinecarboxylate (2.24 g, 9.6 mmol) in THF (10 mL) was added dropwise over 30 min. The mixture was stirred at rt for 20 h, then water was added and the mixture extracted three times with diethylether. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification of the residue by silica gel column chromatography, eluting with a stepwise gradient of 0-10% ethyl acetate in n-heptane, afforded the title compound (0.56 g, 17%) as a colourless oil.

出典