Acetic Acid → 4-Methyl-2-(4-(2-nitro-ethyl)-benzyloxy)pyridine

HRID 77899Notes

Reaction equation

HRID 77899 reaction equation
CS(C)=O.[CH3:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[N+:22]([O-:24])=[O:23])=[CH:16][CH:15]=2)[CH:7]=1.C(O)(=O)C.[BH4-].[Na+]>O>[CH3:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][N+:22]([O-:24])=[O:23])=[CH:16][CH:15]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 592551344-Methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine

Product 1

HCID 592552164-Methyl-2-(4-(2-nitro-ethyl)-benzyloxy)pyridineYield 35.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethyl sulfoxide (50 mL) solution of 4-methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine (3.10 g, 11.5 mmol) described in Manufacturing Example 43-1-3 and acetic acid (3.10 mL) was added sodium borohydride (733 mg, 18.4 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 10 minutes. Water was then added dropwise into the reaction solution at room temperature while cooling appropriately, and the reaction mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5→1:2) to obtain the title compound (1.10 g, 35.1%).

Workup

  1. temperaturewhile cooling appropriately under nitrogen atmosphere
  2. temperaturewhile cooling appropriately
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure
  9. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5→1:2)

Sources & evidence

ORD record
ord-f261aae0b492435397be1de29fced289
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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