Acetic Acid → 2-Benzyloxy-5-(2-nitro-ethyl)pyridine

HRID 640571Notes

Reaction equation

HRID 640571 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[N+:17]([O-:19])=[O:18])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[B-].[Na+].O>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N+:17]([O-:19])=[O:18])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 22959485VertellusHCID 566051462-(Benzyloxy)-5-[(E)-2-nitroethenyl]pyridine

Product 1

HCID 592550692-Benzyloxy-5-(2-nitro-ethyl)pyridineYield 40.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-benzyloxy-5-((E)-2-nitro-vinyl)-pyridine described in Manufacturing Example 231-1-3 (44.0 g, 172 mmol) and acetic acid (44.0 mL) in dimethyl sulfoxide (200 mL) was added sodium borohydrate (11.0 g, 275 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 30 minutes. Water was added to this reaction solution at room temperature while cooling appropriately, which was then partitioned into water and ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4) to obtain the title compound (18.1 g, 40.7%).

Workup

  1. temperaturewhile cooling appropriately under nitrogen atmosphere
  2. temperaturewhile cooling appropriately
  3. customwhich was then partitioned into water and 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=1:4)

Sources & evidence

ORD record
ord-e5243cfbd6be4858a194b163377d9399
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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