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Thiazolidinedione → (5Z)-5-{4-[2-hydroxy-2-(2-methoxyphenyl)ethoxy]benzylidene}-1,3-thiazolidine-2,4-dione

HRID 2274342
ノート
印刷プレビュー

反応式

HRID 2274342 の反応式
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[S:21]1[CH2:25][C:24](=[O:26])[NH:23][C:22]1=[O:27].N1CCCCC1>CCO>[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[C:25]2/[C:24](=[O:26])[NH:23][C:22](=[O:27])[S:21]/2)=[CH:7][CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 866450774-[2-Hydroxy-2-(2-methoxyphenyl)ethoxy]benzaldehyde

生成物 1

HCID 86645078(5Z)-5-{4-[2-hydroxy-2-(2-methoxyphenyl)ethoxy]benzylidene}-1,3-thiazolidine-2,4-dione収率 80.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirring solution of 4-[2-hydroxy-2-(2-methoxyphenyl)ethoxy]benzaldehyde (1.71 g, 6.28 mmol) in absolute EtOH (50 mL) was added 2,4-thiazolidinedione (0.81 g, 6.91 mmol) and piperidine (0.68 mL, 6.9 mmol), and the resulting solution was heated to reflux. The reaction was refluxed overnight and then evaporated in vacuo. The residue was dissolved in EtOAc and this solution was washed with aqueous HOAc (pH 5-6), brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was adsorbed onto silica gel and chromatographed on silica gel eluting with 20-40% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 1.87 g (80%) of the title compound as a light yellow solid. MS (ESI−) for C19H17NO5S m/z 370.1 (M−H)−.

後処理

  1. temperaturethe resulting solution was heated to reflux
  2. temperatureThe reaction was refluxed overnight
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washthis solution was washed with aqueous HOAc (pH 5-6), brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customchromatographed on silica gel eluting with 20-40% EtOAc/DCM
  10. additionFractions containing product
  11. customevaporated in vacuo

出典と根拠

ORDレコード
ord-996e348fc50d49a1b1e8cfa57a354057
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09126959B2

反応ノート

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