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(+)-Camphorquinone → (1s,4r)-1,7,7-Trimethyl-3-[2-(5-methyl-1-phenyl-1h-pyrazol-4-yl)-2-oxo-eth-(e)-ylidene]-bicyclo[2.2.1]heptan-2-one

HRID 2243903
ノート
印刷プレビュー

反応式

HRID 2243903 の反応式
COP([CH2:7][C:8]([C:10]1[CH:11]=[N:12][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]=1[CH3:15])=[O:9])(=O)OC.CC(C)([O-])C.[K+].[CH3:28][C@@:29]12[C:35]([CH3:37])([CH3:36])[C@@H:32]([CH2:33][CH2:34]1)[C:31](=O)[C:30]2=[O:39]>C(O)(C)(C)C>[CH3:28][C@@:29]12[C:35]([CH3:37])([CH3:36])[C@@H:32]([CH2:33][CH2:34]1)/[C:31](=[CH:7]\[C:8]([C:10]1[CH:11]=[N:12][N:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:14]=1[CH3:15])=[O:9])/[C:30]2=[O:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1549179(+)-CamphorquinoneHCID 23665647Potassium tert-butoxideHCID 86609911[2-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-phosphonic acid dimethyl ester

生成物 1

HCID 67364601(1s,4r)-1,7,7-Trimethyl-3-[2-(5-methyl-1-phenyl-1h-pyrazol-4-yl)-2-oxo-eth-(e)-ylidene]-bicyclo[2.2.1]heptan-2-one収率 74.6%

試薬・触媒・溶媒 1

HCID 6386
tert-Butanol
溶媒

実験手順

[2-(5-Methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-phosphonic acid dimethyl ester (1.1 g) in tert-butanol (60 mL) at RT under an argon atmosphere was treated with potassium tert-butoxide (0.412 g) and the mixture was stirred for 30 minutes. Then (1S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]heptane-2,3-dione (0.499 g) was added at RT and the mixture was heated at reflux for 12 h under an argon atmosphere. The reaction mixture was partitioned between water and AcOEt, the layers were separated, the aqueous layer extracted twice with AcOEt. The combined organic layers were washed with water, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/AcOEt 100% to 80%) to give (1S,4R)-1,7,7-trimethyl-3-[2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2-oxo-eth-(E)-ylidene]-bicyclo[2.2.1]heptan-2-one (0.78 g) as a light yellow solid. MS (EI): 348.2 (M+).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 12 h under an argon atmosphere
  3. customThe reaction mixture was partitioned between water and AcOEt
  4. customthe layers were separated
  5. extractionthe aqueous layer extracted twice with AcOEt
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography (heptane/AcOEt 100% to 80%)

出典と根拠

ORDレコード
ord-bf72ccea36c641bda136c57407615c01
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07678795B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート