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

HRID 640339Notes

Reaction equation

HRID 640339 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-5caf64b3d26540eab29c4e27dc6eb4ec
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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