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Dimethylformamide → Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(prop-1-yn-1-yl)benzoate

HRID 2177811
ノート
印刷プレビュー

反応式

HRID 2177811 の反応式
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15](OS(C(F)(F)F)(=O)=O)[C:14](C3C=COC=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:34]#[C:35][CH3:36].C(N[CH:41]([CH3:43])[CH3:42])(C)C.CN([CH:47]=[O:48])C>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:34]#[C:35][CH3:36])[C:14]([C:42]3[CH:41]=[CH:43][O:48][CH:47]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 6335PropyneHCID 7912DiisopropylamineHCID 86677115Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate2 回

生成物 1

HCID 67107923Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(prop-1-yn-1-yl)benzoate

試薬・触媒・溶媒 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418476HCID 178418476、化合物触媒

反応条件

温度
100 °C

実験手順

Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyl-oxy)benzoate (Intermediate 123, 0.2 g), propyne (0.174 g), copper (I) iodide (0.008 g) and bis-(triphenylphosphine)palladium(II) chloride (0.029 g) were added to a solution of diisopropylamine (0.168 g) in DMF (2 ml) in a microwave vial. The mixture was degassed with argon and then heated in the microwave at 100° C. for 1 hour. After cooling, saturated aqueous ammonium chloride solution and ethyl acetate were added. The organic layer was separated, washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 7-25%. The resultant yellow gum was triturated with diethyl ether and the solid was collected by filtration to give methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(prop-1-yn-1-yl)benzoate (0.057 g) as a white solid.

後処理

  1. customThe mixture was degassed with argon
  2. temperatureAfter cooling
  3. additionsaturated aqueous ammonium chloride solution and ethyl acetate were added
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography on silica
  10. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 7-25%
  11. customThe resultant yellow gum was triturated with diethyl ether
  12. filtrationthe solid was collected by filtration

出典と根拠

ORDレコード
ord-24187ef4c68d4da79b93c89ad21a04e1
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09067905B2

反応ノート

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