Sodium hydride → Ethyl 3-(5-hydroxy-1-methyl-1H-indol-3-yl)-2-isopropoxypropionate

HRID 1985426노트

반응식

HRID 1985426 반응식
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:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([CH3:35])[CH:30]=C2C=O)C1C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1.CN(C)C=O.O>[OH:25][C:26]1[CH:34]=[C:33]2[C:32](=[CH:28][CH:27]=1)[N:31]([CH3:35])[CH:30]=[C:15]2[CH2:13][CH:7]([O:25][CH:26]([CH3:27])[CH3:34])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

참가 물질

8

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 122838545-Benzyloxy-1-methylindole-3-carboxaldehydeHCID 22494181Ethyl 2-(diethylphosphoryl)-2-isopropylacetate

생성물 1

HCID 22926993Ethyl 3-(5-hydroxy-1-methyl-1H-indol-3-yl)-2-isopropoxypropionate수율 173.8%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회

실험 절차

3.2 g of Ethyl 2-(diethylphosphoryl)-2-isopropylacetate was dissolved in 25 ml of tetrahydrofuran, and 0.44 g of 60% sodium hydride was added under ice-cooling, and stirring was continued for 20 minutes under ice-cooling. The reaction solution was treated with a solution of 2 g of 5-benzyloxy-1-methyl-1H-indol-3-aldehyde in 5 ml of tetrahydrofuran and 5 ml of N,N-dimethylformamide, and stirred at 50° C. for one hour and then at room temperature for 16 hours. The reaction solution was cooled with ice, treated with water and ammonium chloride solution, 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 20% ethylacetate-hexane was evaporated and the residue was dissolved in 10 ml of ethanol. 0.6 g of 10% Palladium carbon was added to this solution, the atmosphere was replaced with hydrogen, and the mixture was stirred at room temperature for 24 hours. The reaction atmosphere was replaced with nitrogen, the catalyst was filtered off, and the solvent was evaporated. The residue was subjected to silica gel column chromatography (30% ethyl acetate hexane), to give 2 g of the title compound.

후처리

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirred at 50° C. for one hour
  4. waitat room temperature for 16 hours
  5. temperatureThe reaction solution was cooled with ice
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated
  10. washthe fraction eluting with 20% ethylacetate-hexane
  11. customwas evaporated
  12. dissolutionthe residue was dissolved in 10 ml of ethanol
  13. addition0.6 g of 10% Palladium carbon was added to this solution
  14. stirringthe mixture was stirred at room temperature for 24 hours
  15. customThe reaction atmosphere
  16. filtrationthe catalyst was filtered off
  17. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-6c28428224af4d7dbc446d1a22e58779
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544835B2

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