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Hydrochloric Acid → 2-(3,5-Dimethylbiphenyl-4-yl)-4-[1-(tetrahydrofuran-3-yl)methylidene]-cyclopentane-1,3-dione

HRID 509163
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HRID 509163 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:5]=[C:6]([CH3:23])[C:7]=1[C:8]1[C:9](=[O:22])[CH:10]([CH:15](O)[CH:16]2[CH2:20][CH2:19][O:18][CH2:17]2)[CH2:11][C:12]=1[O:13]C.Cl>CC(C)=O>[CH3:23][C:6]1[CH:5]=[C:4]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:3]=[C:2]([CH3:1])[C:7]=1[CH:8]1[C:9](=[O:22])[C:10](=[CH:15][CH:16]2[CH2:20][CH2:19][O:18][CH2:17]2)[CH2:11][C:12]1=[O:13]
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참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 584816012-(3,5-Dimethylbiphenyl-4-yl)-5-[hydroxyl-(tetrahydrofuran-3-yl)-methyl]-3-methoxy-cyclopent-2-enone

생성물 1

HCID 671093232-(3,5-Dimethylbiphenyl-4-yl)-4-[1-(tetrahydrofuran-3-yl)methylidene]-cyclopentane-1,3-dione수율 28.7%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
130 °C

실험 절차

A mixture of 2-(3,5-Dimethylbiphenyl-4-yl)-5-[hydroxyl-(tetrahydrofuran-3-yl)-methyl]-3-methoxy-cyclopent-2-enone (1.1 g, 2.8 mmol), acetone (21 ml) and 2N hydrochloric acid (10 ml) is heated under microwave conditions at 130° C. for 40 minutes. The organic solvent is evaporated under vacuo, diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts are combined, washed with water and brine, dried over anhydrous sodium sulphate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel to give 2-(3,5-dimethylbiphenyl-4-yl)-4-[1-(tetrahydrofuran-3-yl)methylidene]-cyclopentane-1,3-dione (0.29 g).

후처리

  1. customThe organic solvent is evaporated under vacuo
  2. additiondiluted with water (100 ml)
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-83c6a5a6374942c6b5383562e3488258
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096560B2

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