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1-Bromopropane → (Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

HRID 517598
ノート
印刷プレビュー

反応式

HRID 517598 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13](/[CH:14]=[C:15]2/[C:16](=[O:21])[NH:17][C:18](=[O:20])[S:19]/2)=[CH:12][CH:11]=1)[CH3:8].Br[CH2:25][CH2:26][CH3:27]>CN(C=O)C>[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13](/[CH:14]=[C:15]2/[C:16](=[O:21])[N:17]([CH2:25][CH2:26][CH3:27])[C:18](=[O:20])[S:19]/2)=[CH:12][CH:11]=1)[CH3:8]
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 78401-BromopropaneHCID 11430Potassium CarbonateHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

生成物 1

HCID 71697554(Z)-5-(4-ethoxybenzylidene)-3-propylthiazolidine-2,4-dione

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Potassium carbonate (93 mg, 0.60 mmol) was added to a solution of compound 2 (75 mg, 0.30 mmol) in 3 mL of anhydrous DMF at 0° C. After stifling of the reaction mixture for 20 min, a solution of 1-bromopropane (30 μL, 0.33 mmol) in 1 mL of anhydrous DMF was added and then the reaction mixture was stirred at room temperature overnight. The reaction was quenched by adding water and extracted with ethyl acetate. The ethyl acetate layer was washed with water (4×20 mL) and dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (15% ethyl acetate in hexanes) to afford 82 mg (93.9%) as a light-yellow solid.

後処理

  1. customThe reaction was quenched
  2. additionby adding water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water (4×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica column chromatography (15% ethyl acetate in hexanes)
  9. customto afford 82 mg (93.9%) as a light-yellow solid

出典と根拠

ORDレコード
ord-939dcc066a6046ebb1f4f823fb93bf45
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09115122B2

反応ノート

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