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

HRID 2177811
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HRID 2177811 반응식
[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
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참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 6335PropyneHCID 7912DiisopropylamineHCID 86677115Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate2회

생성물 1

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

시약·촉매·용매 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418476HCID 178418476, 화합물촉매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-24187ef4c68d4da79b93c89ad21a04e1
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09067905B2

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