Water → HCID 67136311, 화합물

HRID 230888

반응식

HRID 230888 반응식
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13]([CH:20]=O)=[CH:14][NH:15]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>CS(C)=O.[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13](/[CH:20]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH:14][NH:15]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 24758Sodium hydrideHCID 70158464-(benzyloxy)-1H-indole-3-carbaldehyde

생성물 1

HCID 67136311HCID 67136311, 화합물수율 197.7%

시약·촉매·용매 2

HCID 70671Benzyltriphenylphosphonium chloride촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
65 °C

실험 절차

To a suspension of sodium hydride (60%, 48 mg) in dimethyl sulfoxide (3 mL) was added benzyltriphenylphosphonium chloride (0.47 g), and the mixture was stirred at 65° C. for 1 hour. The reaction mixture was cooled in ice. To the mixture was added 4-benzyloxy-3-formylindole (0.25 g), and the mixture was stirred at 85° C. for 3 hours. The reaction mixture was cooled to room temperature. To the mixture was added water, and the mixture was extracted with ethyl acetate (three times). The extract was washed with water twice, a saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=3/1) to give the title compound (0.32 g).

후처리

  1. temperatureThe reaction mixture was cooled in ice
  2. stirringthe mixture was stirred at 85° C. for 3 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate (three times)
  5. washThe extract was washed with water twice
  6. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=3/1)

출처 및 근거

ORD 기록
ord-a4df83a8600b4fe4971416a94b0c505e
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566699B2

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