Trifluoroacetic acid → HCID 46914013, 화합물

HRID 597846노트

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HRID 597846 반응식
FC(F)(F)[C:3](O)=[O:4].[CH2:8]([O:10][C:11](=[O:24])[CH2:12][CH2:13][C:14]1[C:22]2[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=2[NH:16][CH:15]=1)[CH3:9].COC(OC)OC.[OH-].[Na+]>O.C(OCC)(=O)C>[CH2:8]([O:10][C:11](=[O:24])[CH2:12][CH2:13][C:14]1[C:22]2[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=2[NH:16][C:15]=1[CH:3]=[O:4])[CH3:9]

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 9005Trimethyl orthoformateHCID 14798Sodium HydroxideHCID 46914009HCID 46914009, 화합물

생성물 1

HCID 46914013HCID 46914013, 화합물수율 19%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a trifluoroacetic acid solution (47 mL) containing 3-(3-ethoxy-3-oxopropyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole (4, 10.0 g, 42.5 mmol) was added with trimethylorthoformate (13.6 g, 128 mmol) at 0° C. The reaction was stirred at 0° C. for 30 min, warmed up to room temperature and stirred for 2.0 h. The solution was added with ethyl acetate (250 mL), water (200 mL) and NaOH (18 g). The organic layer was collected and washed with saturated aqueous NaHCO3 (200 mL), dried over MgSO4 (s), and concentrated under reduced pressure. The oily residue was purified by gravity column chromatography (50% EtOAc in hexanes) to give 3-(3-ethoxy-3-oxopropyl)-2-formyl-4-oxo-4,5,6,7-tetrahydro-1H-indole (5, 2.1 g, 8.0 mmol) as yellow solids in 19% yield.

후처리

  1. temperaturewarmed up to room temperature
  2. stirringstirred for 2.0 h
  3. customThe organic layer was collected
  4. washwashed with saturated aqueous NaHCO3 (200 mL)
  5. dry with materialdried over MgSO4 (s)
  6. concentrationconcentrated under reduced pressure
  7. customThe oily residue was purified by gravity column chromatography (50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-9e917815dc6a42dea3435fc387666331
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897602B2

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