反応 #1869180

反応方程式

dimethylsulfoxide

sodium hydride

dimethylsulfoxide

benzyl 4-oxo-1-piperidinecarboxylate

dimethylsulfoxide

water

→

title compound

benzyl 4-methylene-1-piperidinecarboxylate

反応条件

後処理

1. 1
   workup.ADDITIONwas added the reaction mixture
2. 2
   workup.STIRRINGthe mixture was stirred for 1 hour at 50° C
3. 3
   温度After cooling, to the mixture
4. 4
   抽出the mixture was extracted with ethyl acetate (1.5 L)
5. 5
   洗浄The organic layer was washed with a saturated aqueous solution of ammonium chloride (0.5 L)
6. 6
   乾燥a saturated aqueous solution of sodium chloride (0.5 L), dried
7. 7
   濃縮concentrated
8. 8
   その他The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate:chloroform=9:1:1)

実験手順

A sodium hydride (13.2 g) was added to an anhydrous dimethylsulfoxide (176 mL) and the mixture was heated for 2 hours at 60° C. After cooling, to a suspension of methyltriphenylphosphonium bromide (110.4 g) in dimethylsulfoxide (120 mL) was added the reaction mixture, and the mixture was stirred for 30 minutes at room temperature. To the reaction mixture was added a solution of benzyl 4-oxo-1-piperidinecarboxylate (60 g) in dimethylsulfoxide (150 mL), the mixture was stirred for 1 hour at 50° C. After cooling, to the mixture was added water (2.5 L) and the mixture was extracted with ethyl acetate (1.5 L). The organic layer was washed with a saturated aqueous solution of ammonium chloride (0.5 L) and a saturated aqueous solution of sodium chloride (0.5 L), dried and then concentrated. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate:chloroform=9:1:1) to give the title compound (51.1 g) having the following physical data.

出典