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

HRID 1691006Notes

Reaction equation

HRID 1691006 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-389950ae8b3e4f6f8858b621c039db6b
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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