Acetic Acid → 5-Methyl-2-(4-(2-nitro-ethyl)-benzyloxy)pyridine

HRID 1691011Notes

Reaction equation

HRID 1691011 reaction equation
CS(C)=O.[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([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)=[N:10][CH:11]=1.C(O)(=O)C.[BH4-].[Na+]>O>[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([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)=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 592554285-Methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine

Product 1

HCID 592551035-Methyl-2-(4-(2-nitro-ethyl)-benzyloxy)pyridineYield 54.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethyl sulfoxide (40.0 mL) solution of 5-methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine (3.50 g, 12.9 mmol) described in Manufacturing Example 44-1-3 and acetic acid (3.50 mL) was added sodium borohydride (822 mg, 20.6 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 10 minutes. Water was then added dropwise at room temperature while cooling appropriately. The reaction mixture was extracted with ethyl acetate, and the organic layer was 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=1:4) to obtain the title compound (1.91 g, 54.3%).

Workup

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

Sources & evidence

ORD record
ord-3e3489c56075487ca7c3e3666728d9ec
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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