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Piperidine → 5-[4-[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]butylidene]-2,4-oxazolidinedione

HRID 1267300
ノート
印刷プレビュー

反応式

HRID 1267300 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH:25]2OCCCO2)=[CH:18][CH:17]=1.[O:31]1[CH2:35][C:34](=[O:36])[NH:33][C:32]1=[O:37].N1CCCCC1>C(O)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH2:24][CH:25]=[C:35]2[O:31][C:32](=[O:37])[NH:33][C:34]2=[O:36])=[CH:20][CH:21]=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 8082PiperidineHCID 973892,4-OxazolidinedioneHCID 110259022-[3-[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propyl]-1,3-dioxane

生成物 1

HCID 570316105-[4-[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]butylidene]-2,4-oxazolidinedione収率 26%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propyl]-1,3-dioxane (2.0 g), 2,4-oxazolidinedione (0.99 g), piperidine (0.21 g) and acetic acid (50 ml) was heated for 24 hours under reflux. The reaction mixture was concentrated under reduced pressure, to which was added ethyl acetate. The ethyl acetate layer was washed with an aqueous solution of sodium hydrogencarbonate, 2N HCl and water, successively, which was then dried (MgSO4), followed by concentration. The concentrate was purified by means of a silica gel column chromatography. From the fractions eluted with chloroform-ethyl acetate (5:1), 5-[4-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]butylidene]-2,4-oxazolidinedione (0.55 g, 26%) was obtained. Recrystallization from ethyl ether-methanol gave colorless needles, m.p.152-153° C.

後処理

  1. temperaturewas heated for 24 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure, to which
  4. additionwas added ethyl acetate
  5. washThe ethyl acetate layer was washed with an aqueous solution of sodium hydrogencarbonate, 2N HCl and water
  6. dry with materialsuccessively, which was then dried (MgSO4)
  7. concentrationfollowed by concentration
  8. customThe concentrate was purified by means of a silica gel column chromatography
  9. washFrom the fractions eluted with chloroform-ethyl acetate (5:1)

出典と根拠

ORDレコード
ord-28dd0e41658349c9b765015383bb27ca
出典データセット
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06552058B1

反応ノート

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