Thiazolidinedione → 5-{4-[2-(2-Methoxyphenyl)-2-oxoethoxy]benzyl}-1,3-thiazolidine-2,4-dione

HRID 1873821ノート

反応式

HRID 1873821 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>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:2](=[O:1])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][CH:25]2[S:21][C:22](=[O:27])[NH:23][C:24]2=[O:26])=[CH:7][CH:6]=1

参加物

5

反応物 3

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

生成物 1

HCID 252303365-{4-[2-(2-Methoxyphenyl)-2-oxoethoxy]benzyl}-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-a37800e335bb4b43b196358810c5ca01
出典データセット
uspto-grants-2012_11
特許番号
US08304441B2

反応ノート

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