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Piperidine → 5-[3-[4-(2-(5-Methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy)phenyl]propylidene]-2,4-oxazolidinedione

HRID 1377644
ノート
印刷プレビュー

反応式

HRID 1377644 の反応式
O1CCO[CH:2]1[CH2:6][CH2:7][C:8]1[CH:29]=[CH:28][C:11]([O:12][CH2:13][C:14]([C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[O:15])=[CH:10][CH:9]=1.[O:30]1[CH2:34][C:33](=[O:35])[NH:32][C:31]1=[O:36].N1CCCCC1>C(O)(=O)C>[CH3:21][C:20]1[O:19][C:18]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[N:17][C:16]=1[C:14](=[O:15])[CH2:13][O:12][C:11]1[CH:28]=[CH:29][C:8]([CH2:7][CH2:6][CH:2]=[C:34]2[O:30][C:31](=[O:36])[NH:32][C:33]2=[O:35])=[CH:9][CH:10]=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 185461704-[4-[2-(1,3-Dioxolan-2-yl)ethyl]phenoxyacetyl]-5-methyl-2-phenyloxazole

生成物 1

HCID 572491385-[3-[4-(2-(5-Methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy)phenyl]propylidene]-2,4-oxazolidinedione

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 4-[4-[2-(1,3-dioxolan-2-yl) ethyl]phenoxyacetyl]-5-methyl-2-phenyloxazole (1.8 g), 2,4-oxazolidinedione (0.925 g), piperidine (0.12 g) and acetic acid (30 ml) was heated for 15 hours under reflux. The reaction mixture was concentrated under reduced pressure. To the concentrate was added a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform. The chloroform layer was washed with water, dried (MgSO4), followed by distilling off the solvent. The oily residue was subjected to a silica gel column chromatography. From the fractions eluted with methanol-chloroform (1:30, v/v) was obtained 5-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]phenyl]propylidene]-2,4-oxazolidinedione. This compound was dissolved in tetrahydrofuran (THF) (30 ml), to which was added palladium-carbon (5%, 0.3 g). The mixture was subjected to catalytic hydrogenation. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The oily residue was subjected to a silica gel column chromatography. From the fractions eluted with ethyl acetate - hexane (1:1, v/v), 5-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)-2-oxoethoxy]phenyl]propyl]-2,4-oxazolidinedione (0.32 g, 16%) was obtained as an oily product.

後処理

  1. temperaturewas heated for 15 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the concentrate was added a saturated aqueous solution of sodium hydrogencarbonate
  5. extractionfollowed by extraction with chloroform
  6. washThe chloroform layer was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationby distilling off the solvent
  9. washFrom the fractions eluted with methanol-chloroform (1:30, v/v)

出典と根拠

ORDレコード
ord-be50291079b1415d909b588f0478b633
出典データセット
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05665748

反応ノート

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