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

HRID 557262Notes

Reaction equation

HRID 557262 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)pyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine described in Preparation Example 1-3-3 (21.0 g, 81.9 mmol), acetic acid (21 mL) and dimethylsulfoxide (200 mL) was added sodium borohydride (4.96 g, 131 mmol), while being suitably cooled at room temperature. After sodium borohydride was added, the cold bath was removed, the solution was stirred at room temperature for 15 minutes. The reaction solution was partitioned into water and ethyl acetate. The ethyl acetate layer was washed twice with water and once with sodium chloride water, this was dried over anhydrous magnesium sulfate, and the solvent thereof 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).

Workup

  1. customthe cold bath was removed
  2. customThe reaction solution was partitioned into water and ethyl acetate
  3. washThe ethyl acetate layer was washed twice with water and once with sodium chloride water
  4. dry with materialthis was dried over anhydrous magnesium sulfate
  5. customthe solvent thereof 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-5589d36753914bb4b4b3662a9e1649d2
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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