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

HRID 73576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73576
[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 (1.1M) 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-90120c6217b34437bdff400773a4f146
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829193B2

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