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

HRID 1930750Notes

Reaction equation

HRID 1930750 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 and under suitable cooling. After the addition of sodium borohydride, the ice bath was removed and the reaction solution was stirred for 15 minutes at room temperature. The reaction solution was separated into water and ethyl acetate. The ethyl acetate layer was washed twice with water and once with saline, and was then 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 titled compound (16.3 g, 77.1%).

Workup

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

Sources & evidence

ORD record
ord-fe64ffa5f7f94751bb35d901c23559a3
Source dataset
uspto-grants-2012_05
Patent number
US08188119B2

Reaction notes

Loading…