Diisopropylethylamine → Ethyl(6-((2,4-dichlorobenzyl)sulfanyl)-1-benzothiophen-3-yl)acetate

HRID 591487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591487
C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.CCN(C(C)C)C(C)C.[Cl:52][C:53]1[CH:60]=[C:59]([Cl:61])[CH:58]=[CH:57][C:54]=1[CH2:55][SH:56].[CH2:62]([O:64][C:65](=[O:84])[CH2:66][C:67]1[C:71]2[CH:72]=[CH:73][C:74](OS(C(F)(F)F)(=O)=O)=[CH:75][C:70]=2[S:69][CH:68]=1)[CH3:63]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:62]([O:64][C:65](=[O:84])[CH2:66][C:67]1[C:71]2[CH:72]=[CH:73][C:74]([S:56][CH2:55][C:54]3[CH:57]=[CH:58][C:59]([Cl:61])=[CH:60][C:53]=3[Cl:52])=[CH:75][C:70]=2[S:69][CH:68]=1)[CH3:63]

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 957562,4-DichlorobenzenemethanethiolHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57443344Ethyl(6-(((trifluoromethyl)sulfonyl)oxy)-1-benzothiophen-3-yl)acetate

Produkt 1

HCID 118667019Ethyl(6-((2,4-dichlorobenzyl)sulfanyl)-1-benzothiophen-3-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (15.71 mg), DIPEA (0.187 ml), 2,4-dichlorobenzyl mercaptan (0.085 mL) and ethyl(6-(((trifluoromethyl)sulfonyl)oxy)-1-benzothiophen-3-yl)acetate (200 mg) in toluene (6 mL) was added tris(dibenzylideneacetone)dipalladium(0) (24.86 mg) at room temperature. The mixture was refluxed 1.5 h. After cooling, water was poured into mixture, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (238 mg).

Aufarbeitung

  1. temperatureThe mixture was refluxed 1.5 h
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4361cea35fb54252a4bfb996d57628d2
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238639B2

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