Sodium borohydride → HCID 59226486, compound

HRID 73569Notes

Reaction equation

HRID 73569 reaction equation
[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].[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]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 592265443-(3-Nitropyridin-4-yl)cyclohex-2-enone

Product 1

HCID 59226486HCID 59226486, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 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 3-(3-nitropyridin-4-yl)cyclohex-2-enol (99%). LC/MS=221.1 (M+H), LC=2.24 min.

Workup

  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

Sources & evidence

ORD record
ord-5d3ce4be06fd43e188e2e5f5a11ea8fc
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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