Cesium carbonate → Ethyl 5-ethyl-2-(4-nitrophenyl)-1,3-oxazole-4-carboxylate

HRID 43583

反応式

HRID 43583 の反応式
[CH2:1]([C:3]1[O:7][CH:6]=[N:5][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].I[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[CH2:1]([C:3]1[O:7][C:6]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[N:5][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2]

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 124951-Iodo-4-nitrobenzeneHCID 80271Tri-o-tolylphosphineHCID 122141024-Oxazolecarboxylic acid, 5-ethyl-, ethyl ester

生成物 1

HCID 68406117Ethyl 5-ethyl-2-(4-nitrophenyl)-1,3-oxazole-4-carboxylate収率 37.2%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

Dioxane (30 mL) was added to ethyl 5-ethyl-1,3-oxazole-4-carboxylate (described in Armarego, Wilfred L. F.; Taguchi, Hiroyasu; Cotton, Richard G. H.; Battiston, Sandra; Leong, Lillian; Eur. J. Med. Chem. Chim. Ther.; 22; 1987; 283-292, 1.69 g, 10 mmol), 1-iodo-4-nitrobenzene (2.74 g, 11 mmol), palladium acetate (179.6 mg, 0.8 mmol), tris(2-methylphenyl)phosphine (0.49 g, 1.6 mmol) and cesium carbonate (3.25 g, 10 mmol), and the mixture was stirred at 100° C. for 13 hours. Water was added, followed by extraction with ethyl acetate and washing with brine. This was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1, 3/1, 2/1) to obtain 1.08 g of the title compound as a colorless solid (37%).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashing with brine
  3. dry with materialThis was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1, 3/1, 2/1)

出典と根拠

ORDレコード
ord-90ceebe8cc994cf6baf0a2a04633192b
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

関連ノート

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