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Potassium Carbonate → ethyl(6-((E)-2-(2,6-dimethylpyridin-3-yl)vinyl)-1-benzothiophen-3-yl)acetate

HRID 591521
ノート
印刷プレビュー

反応式

HRID 591521 の反応式
C([O-])([O-])=O.[K+].[K+].[CH2:7]([O:9][C:10](=[O:23])[CH2:11][C:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH:21]=O)=[CH:20][C:15]=2[S:14][CH:13]=1)[CH3:8].[Cl-:24].[CH3:25][C:26]1[C:31]([CH2:32][P+:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:30][CH:29]=[C:28]([CH3:52])[N:27]=1>CN(C=O)C>[CH2:7]([O:9][C:10](=[O:23])[CH2:11][C:12]1[C:16]2[CH:17]=[CH:18][C:19](/[CH:21]=[CH:32]/[C:31]3[C:26]([CH3:25])=[N:27][C:28]([CH3:52])=[CH:29][CH:30]=3)=[CH:20][C:15]=2[S:14][CH:13]=1)[CH3:8].[Cl-:24].[CH3:25][C:26]1[C:31]([CH2:32][P+:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:30][CH:29]=[C:28]([CH3:52])[N:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 118656271((2,6-Dimethylpyridin-3-yl)methyl)(triphenyl)phosphonium chlorideHCID 131734528Ethyl(6-formyl-1-benzothiophen-3-yl)acetate

生成物 2

HCID 89775432ethyl(6-((E)-2-(2,6-dimethylpyridin-3-yl)vinyl)-1-benzothiophen-3-yl)acetateHCID 118656271((2,6-Dimethylpyridin-3-yl)methyl)(triphenyl)phosphonium chloride

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of K2CO3 (134 mg), ethyl(6-formyl-1-benzothiophen-3-yl)acetate (160 mg), ((2,6-dimethylpyridin-3-yl)methyl) (triphenyl)phosphonium chloride (323 mg) and DMF (5 mL) was stirred at room temperature for 3 d. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give ethyl(6-((E)-2-(2,6-dimethylpyridin-3-yl)vinyl)-1-benzothiophen-3-yl)acetate (example 179, 60 mg) and ethyl(6-((Z)-2-(2,6-dimethylpyridin-3-yl)vinyl)-1-benzothiophen-3-yl)acetate (example 180, 110 mg).

後処理

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  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-b32954b935b64ccba76a58ff8a27a0f3
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238639B2

反応ノート

読み込み中…

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