Carbon Dioxide → 4-Methoxycarbonyl-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole)

HRID 1108170ノート

反応式

HRID 1108170 の反応式
[CH3:1][C:2]1([CH3:16])[S:6][C:5]2[CH:7]=[C:8]3[S:12][C:11]([CH3:14])([CH3:13])[S:10][C:9]3=[CH:15][C:4]=2[S:3]1.C([Li])CCC.[C:22](=[O:24])=[O:23].[C:25](=O)([O-])[O-].[K+].[K+].CI>CCOCC.CN(C=O)C>[CH3:25][O:23][C:22]([C:15]1[C:4]2[S:3][C:2]([CH3:16])([CH3:1])[S:6][C:5]=2[CH:7]=[C:8]2[S:12][C:11]([CH3:14])([CH3:13])[S:10][C:9]=12)=[O:24]

参加物

8

反応物 5

HCID 280Carbon DioxideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 111969402,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithioleHCID 178418339Butyllithium

生成物 1

HCID 539241844-Methoxycarbonyl-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole)

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole (2.0 g, 6.98 mmol) was dissolved in dry ether (50.0 mL) in a dry, argon filled reaction flask. n-Butyllithium (3.07 mL, 2.5M in hexane) was added and the reaction mixture was stirred for 30 min. The solution was poured onto solid carbon dioxide and, after stirring overnight, the ether was filtered off. The solid residue was washed with chloroform and dried under vacuum. The crude product was mixed with potassium carbonate (0.97 g, 6.98 mmol) in dry DMF (20.0 mL) and was stirred for 1.5 h at 60° C. After cooling to ambient temperature, methyl iodide (0.435 mL, 6.98 mmol) was added. The stirring was continued overnight. The mixture was filtered, the solution evaporated and the residue was dissolved in dichloromethane and water. The organic phase was washed with water (2*30 mL), dried (Na2SO4) and evaporated to give after additional drying under vacuum a bright green-yellow crystalline pure product. Yield 1.56 g (65%).

後処理

  1. additionfilled
  2. customreaction flask
  3. stirringafter stirring overnight
  4. filtrationthe ether was filtered off
  5. washThe solid residue was washed with chloroform
  6. customdried under vacuum
  7. stirringwas stirred for 1.5 h at 60° C
  8. waitThe stirring was continued overnight
  9. filtrationThe mixture was filtered
  10. customthe solution evaporated
  11. dissolutionthe residue was dissolved in dichloromethane
  12. washThe organic phase was washed with water (2*30 mL)
  13. dry with materialdried (Na2SO4)
  14. customevaporated
  15. customto give
  16. customafter additional drying under vacuum a bright green-yellow crystalline pure product

出典と根拠

ORDレコード
ord-4267caa3585c4426925b341e6bfe4b5d
出典データセット
uspto-grants-2000_05
特許番号
US06063360

反応ノート

読み込み中…