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

HRID 1920213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1920213
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b409db2910244002864b8514b348b431
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168794B2

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