Nitromethane → 1-p-Fluorobenzyl-2-nitromethylene-pyrrolidine

HRID 426952

反応式

HRID 426952 の反応式
S(OC)(OC)(=O)=O.[F:8][C:9]1[CH:21]=[CH:20][C:12]([CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=O)=[CH:11][CH:10]=1.C[O-].[Na+].[Na].[N+:26]([CH3:29])([O-:28])=[O:27]>O.CO>[F:8][C:9]1[CH:21]=[CH:20][C:12]([CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[CH:29][N+:26]([O-:28])=[O:27])=[CH:11][CH:10]=1

参加物

8

反応物 5

HCID 6375NitromethaneHCID 6497Dimethyl SulfateHCID 30454462-Pyrrolidinone, 1-((4-fluorophenyl)methyl)-HCID 5360545SodiumHCID 10942334Sodium Methoxide

生成物 1

HCID 540091111-p-Fluorobenzyl-2-nitromethylene-pyrrolidine収率 55.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

26.1 g (0.207 mol) of dimethyl sulphate are added to 40 g (0.207 mol) of 1-p-fluorobenzyl-pyrrolidin-2-one and the mixture is heated to 60° for 4 hours. It is then cooled and a solution of sodium methylate prepared from 4.75 g (0.207 gram atom) of sodium and 100 ml of methanol is introduced slowly, at 0°. When the addition is complete, the mixture is stirred for 30 minutes at 50° C. and again cooled to 0°, and 18.9 g (0.31 mol) of nitromethane are added dropwise whilst continuing the stirring. The reaction mixture is left at ambient temperature for 12 hours and is then heated to 50° for 2 hours. It is cooled, and poured into 500 ml of water, which are then extracted with chloroform. The organic layer is now separated off, washed with water and dried over magnesium sulphate, and the solvent is driven off. The residual product is washed with ether and recrystallised from ethanol. 27 g (55.2% yield) of 1-p-fluorobenzyl-2-nitromethylene-pyrrolidine are thus collected in the form of light yellow crystals melting at 108.5°-109°.

後処理

  1. temperaturethe mixture is heated to 60° for 4 hours
  2. temperatureIt is then cooled
  3. additionis introduced slowly, at 0°
  4. additionWhen the addition
  5. temperatureagain cooled to 0°
  6. waitThe reaction mixture is left at ambient temperature for 12 hours
  7. temperatureis then heated to 50° for 2 hours
  8. temperatureIt is cooled
  9. extractionare then extracted with chloroform
  10. customThe organic layer is now separated off
  11. washwashed with water
  12. dry with materialdried over magnesium sulphate
  13. washThe residual product is washed with ether
  14. customrecrystallised from ethanol

出典と根拠

ORDレコード
ord-d0cfedf70e894672bed7d8a50dcaf016
出典データセット
uspto-grants-1979_10
特許番号
US04172143

関連ノート

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