Cerium(III) chloride → HCID 59226486、化合物

HRID 924409ノート

反応式

HRID 924409 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 59226486HCID 59226486、化合物収率 55.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-eca8f2868b0140bcb8477c85625c7956
出典データセット
uspto-grants-2016_03
特許番号
US09278950B2

反応ノート

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