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

HRID 509163
ノート
印刷プレビュー

反応式

HRID 509163 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
130 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-83c6a5a6374942c6b5383562e3488258
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096560B2

反応ノート

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