Cerium(III) chloride → HCID 59226486, 화합물

HRID 924409노트

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HRID 924409 반응식
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH:11]=1)([O-:3])=[O:2].[Cl-].[Cl-].[Cl-].[Ce+3].[BH4-].[Na+]>CCO>[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][CH2:14][CH2:13][CH:12]([OH:16])[CH:11]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 592265443-(3-Nitropyridin-4-yl)cyclohex-2-enone

생성물 1

HCID 59226486HCID 59226486, 화합물수율 55.3%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

To a solution of 3-(3-nitropyridin-4-yl)cyclohex-2-en-1-one (1.9 g, 8.7 mmol) and cerium trichloride (4.2 g, 11 mmol) in EtOH (30 mL) at 0° C., sodium tetrahydroborate (0.43 g, 11 mmol) was slowly added. The reaction mixture was stirred at 0° C. for 2 h, then quenched with water (40 mL). After vacuum filtration, the residue was diluted with EtOAc. The aqueous layer was extracted three times with EtOAc. The combined organic layers were dried, filtered and concentrated under reduced pressure to give a crude product, which was further purified by silica gel column chromatography (eluting with 0-30% MeOH in EtOAc) to give the sub-title compound (1.06 g, 55%). LCMS calc. for C11H13NO3 (M+H)+: m/z=221.1. Found: 221.1.

후처리

  1. customquenched with water (40 mL)
  2. filtrationAfter vacuum filtration
  3. additionthe residue was diluted with EtOAc
  4. extractionThe aqueous layer was extracted three times with EtOAc
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a crude product, which
  9. customwas further purified by silica gel column chromatography (eluting with 0-30% MeOH in EtOAc)

출처 및 근거

ORD 기록
ord-eca8f2868b0140bcb8477c85625c7956
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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