Acetic Acid → 2-(2-Fluoro4-(2-nitro-ethyl)-phenoxymethyl)pyridine

HRID 78056Notes

Reaction equation

HRID 78056 reaction equation
CS(C)=O.[F:5][C:6]1[CH:19]=[C:18](/[CH:20]=[CH:21]/[N+:22]([O-:24])=[O:23])[CH:17]=[CH:16][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C(O)(=O)C.[BH4-].[Na+]>O>[F:5][C:6]1[CH:19]=[C:18]([CH2:20][CH2:21][N+:22]([O-:24])=[O:23])[CH:17]=[CH:16][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 592551412-(2-Fluoro-4-((E)-2-nitro-vinyl)-phenoxymethyl)pyridine

Product 1

HCID 592550802-(2-Fluoro4-(2-nitro-ethyl)-phenoxymethyl)pyridineYield 49.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethyl sulfoxide (30.0 mL) solution of 2-(2-fluoro-4-((E)-2-nitro-vinyl)-phenoxymethyl)-pyridine (3.00 g, 10.9 mmol) described in Manufacturing Example 87-1-2 and acetic acid (3.00 mL) was added sodium borohydride (660 mg, 17.4 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 20 minutes at room temperature. Water was then added dropwise at room temperature while cooling appropriately. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was crystallized with a tetrahydrofuran-ethyl acetate-heptane system and filtered to obtain the title compound (1.50 g, 49.8%).

Workup

  1. temperaturewhile cooling appropriately under nitrogen atmosphere
  2. temperaturewhile cooling appropriately
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was crystallized with a tetrahydrofuran-ethyl acetate-heptane system
  9. filtrationfiltered

Sources & evidence

ORD record
ord-669ba9c077c8414693842d2792628ad7
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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