Sodium hydride → Tert-butyl 5-(3-ethoxy-2-isopropoxy-3-oxo-1-propenyl)-2-methoxybenzoate

HRID 1816557ノート

反応式

HRID 1816557 の反応式
C(P([CH:7](C(C)C)[C:8]([O:10][CH2:11][CH3:12])=[O:9])(CC)=O)C.[H-].[Na+].[CH:18]([C:20]1[CH:21]=[CH:22][C:23]([O:33][CH3:34])=[C:24]([CH:32]=1)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=O.[Cl-].[NH4+]>O1CCCC1>[CH2:11]([O:10][C:8](=[O:9])[C:7]([O:27][CH:28]([CH3:30])[CH3:29])=[CH:18][C:20]1[CH:21]=[CH:22][C:23]([O:33][CH3:34])=[C:24]([CH:32]=1)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:12]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22494181Ethyl 2-(diethylphosphoryl)-2-isopropylacetateHCID 22494361Tert-butyl 5-formyl-2-methoxybenzoate

生成物 1

HCID 69800512Tert-butyl 5-(3-ethoxy-2-isopropoxy-3-oxo-1-propenyl)-2-methoxybenzoate収率 162.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1.6 g of ethyl 2-(diethylphosphoryl)-2-isopropylacetate was dissolved in 30 ml tetrahydrofuran, and 0.24 g of 60% sodium hydride was added thereto under ice-cooling. After stirring the reaction solution for 30 minutes under ice-cooling, 1.2 g of tert-butyl 5-formyl-2-methoxybenzoate was added, followed by stirring at room temperature for 3 hours. Aqueous ammonium chloride solution was added to the reaction mixture, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (3:1), 1.5 g of tert-butyl 5-(3-ethoxy-2-isopropoxy-3-oxo-1-propenyl)-2-methoxybenzoate was obtained as an E-Z mixture.

後処理

  1. temperatureunder ice-cooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 3 hours
  4. extractionby extracting with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. washfrom fractions eluted with hexane-ethyl acetate (3:1)

出典と根拠

ORDレコード
ord-a678795e259b49d3889fa60c66fb0c67
出典データセット
uspto-grants-2005_04
特許番号
US06884821B1

反応ノート

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