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Ethyl Acetate → Ethyl 1-(2-fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

HRID 1428084
ノート
印刷プレビュー

反応式

HRID 1428084 の反応式
CC1C=CC(S(O[CH2:12][CH2:13][F:14])(=O)=O)=CC=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23](=[O:33])[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][NH:26][CH:27]=2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C=O)C>[F:14][CH2:13][CH2:12][N:26]1[CH:27]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=2)[C:23](=[O:33])[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 66771917Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

生成物 1

HCID 86700035Ethyl 1-(2-fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate収率 29.8%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
80 °C

実験手順

2-Fluoroethyl 4-methylbenzenesulfonate (1.00 g) was added to a suspension of ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (1.00 g) and cesium carbonate (2.49 g) in DMF (9 ml) at room temperature. The reaction mixture was stirred at 80° C. for two hours. The reaction mixture was returned to room temperature and diluted by adding ethyl acetate. The organic layer was washed with water and brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, the residue was purified by silica gel column chromatography [ethyl acetate:hexane:methanol=1:1:0->7:3:0->1:0:0->19:0:1 (v/v)] to give 0.35 g of the title compound as an oily substance.

後処理

  1. customwas returned to room temperature
  2. additiondiluted
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography [ethyl acetate:hexane:methanol=1:1:0->7:3:0->1:0:0->19:0:1 (v/v)]

出典と根拠

ORDレコード
ord-9bc181e7c7004466a32dcb752ea23d18
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933103B2

反応ノート

読み込み中…

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