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

HRID 43583

반응식

HRID 43583 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-90ceebe8cc994cf6baf0a2a04633192b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536197B2

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