Cesium carbonate → 3-(2-Oxooxazolidin-3-yl)benzoic Acid Methyl Ester

HRID 1612441ノート

反応式

HRID 1612441 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[O:18]1[CH2:22][CH2:21][NH:20][C:19]1=[O:23].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([N:20]2[CH2:21][CH2:22][O:18][C:19]2=[O:23])[CH:3]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 12070Methyl 3-bromobenzoateHCID 739492-OxazolidinoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

生成物 1

HCID 695897133-(2-Oxooxazolidin-3-yl)benzoic Acid Methyl Ester収率 21.9%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

Methyl 3-bromobenzoate (500 mg, 2.33 mmol), caesium carbonate (1.06 g, 3.26 mmol), oxazolidin-2-one (243 mg, 2.80 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (107 mg, 0.186 mmol) and tris(dibenzylideneacetone)dipalladium (0) (43 mg, 0.047 mmol) were refluxed under argon in dioxane (6 ml) for 18 h. After cooling, the mixture was filtered and evaporated in vacuo. Column chromatography on silica gel eluting with a gradient of 10–50% ethyl acetate in hexane gave the title compound (113 mg).

後処理

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customevaporated in vacuo

出典と根拠

ORDレコード
ord-5fc2000416bf4e678773e8b3eb663a12
出典データセット
uspto-grants-2006_01
特許番号
US06992103B2

反応ノート

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