Nitroethane → 2-Nitro-1-pyridin-4-yl-propan-1-ol

HRID 2220738Notes

Reaction equation

HRID 2220738 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[N+:9]([CH2:12][CH3:13])([O-:11])=[O:10].[OH-].[Na+]>CCO.O>[N+:9]([CH:12]([CH3:13])[CH:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[OH:8])([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 6587NitroethaneHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 2229572-Nitro-1-pyridin-4-yl-propan-1-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.0 eq. of 4-pyridinecarboxaldehyde (63, Aldrich, cat. no. P6,240-2) and 1.5 eq of nitroethane (Aldrich, cat. no. 22,787-0) in absolute EtOH was stirred at 0° C. as a solution of 2.0 eq. of NaOH in water was added. After a time sufficient for reaction completion, the reaction mixture was concentrated by rotary evaporation and neutralized (pH 7-8) with conc. HCl. A white precipitate formed. The mixture was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and the solvent removed by rotary evaporation. The material was purified by flash chromatography on silica gel using a mixture of MeOH—CH2Cl2 as eluant to afford 64 as a mixture of diastereomers.

Workup

  1. additionwas added
  2. customAfter a time sufficient for reaction completion
  3. concentrationthe reaction mixture was concentrated by rotary evaporation and neutralized (pH 7-8) with conc. HCl
  4. customA white precipitate formed
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed by rotary evaporation
  9. customThe material was purified by flash chromatography on silica gel using
  10. additiona mixture of MeOH—CH2Cl2 as eluant

Sources & evidence

ORD record
ord-7b71aeab98dc4171bcbc4f3cf3a99000
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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