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

HRID 73570Notes

Reaction equation

HRID 73570 reaction equation
[CH3:1][C:2]1([CH3:18])[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+]>CO>[CH3:1][C:2]1([CH3:18])[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

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 592264755,5-Dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone

Product 1

HCID 592264895,5-Dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enolYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone (1.0 eq), and CeCl3-7H2O (1.2 eq) in MeOH (0.2 M) was added NaBH4 (1.0 eq) at 0° C. The solution was stirred for 1 hour, and then quenched by 5 mL of water. The volatiles were removed in vacuum and the residue was partitioned between EtOAc and H2O. The organic layer was separated and washed with brine. The combined aqueous was back extracted with EtOAc and the organic was washed with brine. The combined organics were dried over MgSO4, filtered and concentrated. The residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes) to give 5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol (74%). LC/MS (m/z): MH+=249.2, Rt=0.76 min.

Workup

  1. customquenched by 5 mL of water
  2. customThe volatiles were removed in vacuum
  3. customthe residue was partitioned between EtOAc and H2O
  4. customThe organic layer was separated
  5. washwashed with brine
  6. extractionThe combined aqueous was back extracted with EtOAc
  7. washthe organic was washed with brine
  8. dry with materialThe combined organics were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-d67a1769f03b40719540626151b25157
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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