2-Piperidone → 1-(Tetrahydro-2-oxo-3-furyl)-2-piperidinone

HRID 27406

反応式

HRID 27406 の反応式
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9].Br[CH:11]1[CH2:15][CH2:14][O:13][C:12]1=[O:16]>C1C=CC=CC=1.CN(C)C=O>[O:16]=[C:12]1[CH:11]([N:3]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]2=[O:9])[CH2:15][CH2:14][O:13]1

参加物

6

反応物 3

HCID 126652-PiperidoneHCID 24758Sodium hydrideHCID 954632(3H)-Furanone, 3-bromodihydro-

生成物 1

HCID 233428711-(Tetrahydro-2-oxo-3-furyl)-2-piperidinone収率 107%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
60 °C

実験手順

1.25 g (0.05 mol) of sodium hydride (2.5 g of a 50% commercial suspension in paraffin, previously washed twice with benzene) are suspended in 50 ml of anhydrous N,N-dimethylformamide. A solution of 4.95 g (0.05 mol) of 2-piperidinone in 20 ml of N,N-dimethylformamide is added dropwise to the suspension. The mixture is then heated to 60° C. until no more gas is evolved, whereafter it is cooled. A solution of 8.25 g (0.05 mol) of 3-bromodihydro-2(3H)-furanone in 20 ml of anhydrous N,N-dimethylformamide is added dropwise while keeping the temperature at 5° to 10° C. The mixture is then stirred at 60° C. for 5 hours. N,N-Dimethylformamide is evaporated off under reduced pressure. The residue is taken up in chloroform and the insoluble matter filtered off on Norit. The filtrate is again evaporated and 9.8 g of a heavy syrup are obtained. Mass spectrum: M+. at 183 m/e.

後処理

  1. temperatureis cooled
  2. customat 5° to 10° C
  3. customN,N-Dimethylformamide is evaporated off under reduced pressure
  4. filtrationthe insoluble matter filtered off on Norit
  5. customThe filtrate is again evaporated

出典と根拠

ORDレコード
ord-d71a5e4b990c4897a490adf4f3bc69d3
出典データセット
uspto-grants-1980_09
特許番号
US04221789

関連ノート

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