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

HRID 591521
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HRID 591521 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b32954b935b64ccba76a58ff8a27a0f3
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238639B2

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