Acetic Acid → 2-(4-(2-Nitro-ethyl)-phenoxy)-pyridine

HRID 1891957Notes

Reaction equation

HRID 1891957 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:18]=[CH:17][C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=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:18]=[CH:17][C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:8][CH:7]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 592552602-(4-((E)-2-Nitro-vinyl)-phenoxy)-pyridine

Product 1

HCID 592552412-(4-(2-Nitro-ethyl)-phenoxy)-pyridineYield 45%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-(4-((E)-2-nitro-vinyl)-phenoxy)-pyridine (9.9 g, 41 mmol) described in Manufacturing Example 209-1-2, acetic acid (2.5 g) and dimethyl sulfoxide (60 mL) was added sodium borohydride (770 mg, 20 mmol) while the temperature was held at 30° C. or lower, which was stirred for 15 minutes at room temperature. This reaction solution was partitioned into ethyl acetate and water while the temperature was held at 30° C. or lower. The organic layer was separated and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the title compound (4.5 g, 45%).

Workup

  1. customwas held at 30° C.
  2. customThis reaction solution was partitioned into ethyl acetate and water while the temperature
  3. customwas held at 30° C.
  4. customThe organic layer was separated
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-ff578b12033f4942901f73ab70124d6e
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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