Ethyl bromoacetate → ethyl [1-hexyl-3-(6-hydroxy-1,3-benzodioxol-5-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetate

HRID 545748노트

반응식

HRID 545748 반응식
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]([C:28]2[C:36]([OH:37])=[CH:35][C:31]3[O:32][CH2:33][O:34][C:30]=3[CH:29]=2)[C:20]1=[O:38])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Br[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]>C1COCC1>[CH2:13]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])([C:28]2[C:36]([OH:37])=[CH:35][C:31]3[O:32][CH2:33][O:34][C:30]=3[CH:29]=2)[C:20]1=[O:38])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

6

반응물 4

HCID 7748Ethyl bromoacetateHCID 7912DiisopropylamineHCID 588725471-hexyl-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-oneHCID 178418339Butyllithium

생성물 1

HCID 58872453ethyl [1-hexyl-3-(6-hydroxy-1,3-benzodioxol-5-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetate수율 8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-75 °C

실험 절차

To a solution of diisopropylamine (1.14 g, 11.0 mmol) in THF (10.0 mL) was added n-butyl lithium (7.00 mL, 11.0 mmol, 1.6 M solution in hexane) at −75° C. The resulting mixture was stirred at −75° C. for half an hour and added slowly to a solution of 1-hexyl-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one in THF (20.0 mL) at −75° C. After stirring at −75° C. for another half an hour, ethyl bromoacetate was added. The mixture was stirred at ambient temperature for 18 hrs and quenched with saturated ammonium chloride solution. The organic solvent was removed in vacuo and the aqueous residue was diluted with ethyl acetate (100 mL). The organic layer was washed with saturated ammonium chloride (25.0 mL), brine (50.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography eluting with 40% EtOAc/Hexanes to yield the title compound (0.19 g, 8%) as an oil: MS (ES+) m/z 440.5 (M+1).

후처리

  1. stirringAfter stirring at −75° C. for another half an hour
  2. stirringThe mixture was stirred at ambient temperature for 18 hrs
  3. customquenched with saturated ammonium chloride solution
  4. customThe organic solvent was removed in vacuo
  5. additionthe aqueous residue was diluted with ethyl acetate (100 mL)
  6. washThe organic layer was washed with saturated ammonium chloride (25.0 mL), brine (50.0 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo to dryness
  10. washeluting with 40% EtOAc/Hexanes

출처 및 근거

ORD 기록
ord-45606b373ec746dcaa8a80d5fa7767bc
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935721B2

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