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

HRID 591487ノート

反応式

HRID 591487 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4361cea35fb54252a4bfb996d57628d2
出典データセット
uspto-grants-2016_01
特許番号
US09238639B2

反応ノート

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