Acetic Acid → 2-((4-(2-Nitroethyl)benzyl)oxy)pyridine

HRID 1894676Notes

Reaction equation

HRID 1894676 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:19]=[CH:18][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][CH:7]=1)([O-:3])=[O:2].C(O)(=O)C.[BH4-].[Na+]>CS(C)=O>[N+:1]([CH2:4][CH2:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][CH:7]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydride2×HCID 58076258(E)-2-((4-(2-Nitrovinyl)benzyl)oxy)pyridine

Product 1

HCID 580762662-((4-(2-Nitroethyl)benzyl)oxy)pyridineYield 77.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine (21.0 g, 81.9 mmol) described in Manufacturing Example 1-1-3, acetic acid (21 mL), and dimethyl sulfoxide (200 mL) was added sodium borohydride (4.96 g, 131 mmol) at room temperature while cooling suitably. After the addition of the sodium borohydride, the ice bath was removed, followed by stirring for 15 minutes at room temperature. The reaction solution was separated into water and ethyl acetate. The ethyl acetate layer was washed with water twice and with saline once, and this product was dried over anhydrous magnesium sulfate and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3) to obtain the title compound (16.3 g, 77.1%).

Workup

  1. temperaturewhile cooling suitably
  2. customthe ice bath was removed
  3. customThe reaction solution was separated into water and ethyl acetate
  4. washThe ethyl acetate layer was washed with water twice
  5. dry with materialwith saline once, and this product was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3)

Sources & evidence

ORD record
ord-ada74513ce9544919c62baa4f602facc
Source dataset
uspto-grants-2013_08
Patent number
US08513287B2

Reaction notes

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