Sodium borohydride → 5-Methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol

HRID 1920213노트

반응식

HRID 1920213 반응식
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:3]1.[BH4-].[Na+]>CCO>[CH3:1][CH:2]1[CH2:7][CH:6]([OH:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:3]1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 592265435-Methyl-3-(3-nitro-4-pyridinyl)-2-cyclohexen-1-one

생성물 1

HCID 671307105-Methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol수율 91%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

To a solution of 5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone (1.0 equiv.) was added EtOH (1.1 M) and CeCl3-7H2O (1.3 equiv.). The reaction was cooled to 0° C., then NaBH4 (1.3 equiv.) was added in portions. Stirred for 2 h at 0° C., then quenched by adding water, concentrated to remove the EtOH, added EtOAc, extracted the organics, dried with brine, then Na2SO4, and concentrated to yield 5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol (91%). LC/MS=235.2 (M+H), LC=2.62 min.

후처리

  1. customquenched
  2. additionby adding water
  3. concentrationconcentrated
  4. customto remove the EtOH
  5. additionadded EtOAc
  6. extractionextracted the organics,
  7. dry with materialdried with brine
  8. concentrationNa2SO4, and concentrated

출처 및 근거

ORD 기록
ord-b409db2910244002864b8514b348b431
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168794B2

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