Dimethyl Sulfoxide → 2-(4-(2-Nitro-ethyl)-phenoxymethyl)-pyridine

HRID 1694179Notes

Reaction equation

HRID 1694179 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:19]=[CH:18][C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][CH:7]=1)([O-:3])=[O:2].CS(C)=O.[BH4-].[Na+]>C(O)(=O)C>[N+:1]([CH2:4][CH2:5][C:6]1[CH:19]=[CH:18][C:9]([O:10][CH2:11][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 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 592551952-(4-((E)-Nitro-vinyl)-phenoxymethyl)-pyridine

Product 1

HCID 592555222-(4-(2-Nitro-ethyl)-phenoxymethyl)-pyridineYield 20%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(4-((E)-nitro-vinyl)-phenoxymethyl)-pyridine (33.9 g, 132 mmol) described in Manufacturing Example 203-1-2 in acetic acid (34 mL) and dimethyl sulfoxide (576 mL) was added sodium borohydride (7.99 g, 211 mmol) at room temperature while cooling appropriately. This mixture was stirred for 5 hours at room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was recrystallized from heptane and ethyl acetate to obtain the title compound (6.81 g, 20%).

Workup

  1. temperaturewhile cooling appropriately
  2. customThis mixture was partitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was recrystallized from heptane and ethyl acetate

Sources & evidence

ORD record
ord-ba8cab08715a4087960de195b4102333
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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