Pyridine → Des-(2-cyclohexane-1,3-dione) Fenquinotrione Ethyl Ester

HRID 240355ノート

反応式

HRID 240355 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6](=[O:12])[NH:7]2.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](OB(O)O)=[CH:22][CH:21]=1.N1C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CCCCCC.C(OCC)(=O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6](=[O:12])[N:7]2[C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1

参加物

9

反応物 4

HCID 1049PyridineHCID 8471TriethylamineHCID 147699944-Methoxyphenyl boric acidHCID 67531483Ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

生成物 1

HCID 67533339Des-(2-cyclohexane-1,3-dione) Fenquinotrione Ethyl Ester収率 78%

試薬・触媒・溶媒 4

HCID 8895Cupric acetate触媒HCID 6212Chloroform溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a slurry containing 5.7 g (22.6 mmol) of ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylate, 6.9 g (45.4 mmol) of 4-methoxyphenylboric acid, 8.2 g (45.1 mmol) of anhydrous copper (II) acetate and chloroform (200 ml), 3.6 g (45.5 mmol) of pyridine and 4.6 g (45.5 mmol) of triethylamine were added dropwise, and the mixture was stirred for 72 hours at room temperature. The reaction mixture was washed with 10% hydrochloric acid, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was isolated by silica gel chromatography (developing solvent: ethyl acetate:hexane=2:3), and the isolated solid was washed with diisopropyl ether, to obtain 6.3 g (yield: 78%) of ethyl 5-chloro-1-(4-methoxyphenyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate as a pale yellow powder.

後処理

  1. additionwere added dropwise
  2. washThe reaction mixture was washed with 10% hydrochloric acid
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. washthe isolated solid was washed with diisopropyl ether

出典と根拠

ORDレコード
ord-9ae5fae523844b15b5eaaa0a82285c02
出典データセット
uspto-grants-2014_02
特許番号
US08648075B2

反応ノート

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