Sodium hydride → Ethyl 3-(4-hydroxyphenyl)-2-isopropoxypropanoate

HRID 1985424ノート

反応式

HRID 1985424 の反応式
C(P([CH:7]([CH:13]([CH3:15])C)[C:8]([O:10][CH2:11][CH3:12])=[O:9])(CC)=O)C.[H-].[Na+].C([O:25][C:26]1[CH:33]=[CH:32]C(C=O)=[CH:28][CH:27]=1)C1C=CC=CC=1>O1CCCC1.CN(C)C=O.O>[OH:25][C:26]1[CH:27]=[CH:28][C:15]([CH2:13][CH:7]([O:25][CH:26]([CH3:33])[CH3:27])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:32][CH:33]=1

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 22494181Ethyl 2-(diethylphosphoryl)-2-isopropylacetate

生成物 1

HCID 22926879Ethyl 3-(4-hydroxyphenyl)-2-isopropoxypropanoate収率 151.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

5.2 g of Ethyl 2-(diethylphosphoryl)-2-isopropylacetate was dissolved in 40 ml of tetrahydrofuran, and 0.53 g of 60% sodium hydride was added under ice-cooling, and the mixture was stirred for 20 minutes under ice-cooling. The reaction solution was treated with a solution of 3.0 g of 4-benzyloxybenzaldehyde in 15 ml of tetrahydrofuran and 10 ml of N,N-dimethylformamide, and stirred at room temperature for 16 hours. The reaction solution was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated. The residue was subjected to silica gel column chromatography, and the fraction eluting with 5% ethyl acetate-hexane was concentrated. The residue was dissolved in 40 ml of ethanol, and 0.4g of 10% palladium carbon was added, the atmosphere was replaced with hydrogen, and the mixture was stirred at room temperature for 5 hours. Then, the atmosphere was replaced with nitrogen, the catalyst was filtered off, and the solvent was evaporated. The residue was subjected to silica gel column chromatography (20% ethyl acetate-hexane), to give 2.7 g of the title compound.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirred at room temperature for 16 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. washthe fraction eluting with 5% ethyl acetate-hexane
  9. concentrationwas concentrated
  10. dissolutionThe residue was dissolved in 40 ml of ethanol
  11. addition0.4g of 10% palladium carbon was added
  12. stirringthe mixture was stirred at room temperature for 5 hours
  13. filtrationthe catalyst was filtered off
  14. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-972e701db86a4a3ab4a76f5a9bc81378
出典データセット
uspto-grants-2009_06
特許番号
US07544835B2

反応ノート

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