Acetic Acid → 2-((4-(2-Nitroethyl)benzyl)oxy)pyridine

HRID 1894680Notes

Reaction equation

HRID 1894680 reaction equation
CS(C)=O.C(O)(=O)C.[N+:9](/[CH:12]=[CH:13]/[C:14]1[CH:27]=[CH:26][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:16][CH:15]=1)([O-:11])=[O:10].[BH4-].[Na+]>C(OCC)C.C(OCC)(=O)C.O>[N+:9]([CH2:12][CH2:13][C:14]1[CH:27]=[CH:26][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:16][CH:15]=1)([O-:11])=[O:10]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 58076258(E)-2-((4-(2-Nitrovinyl)benzyl)oxy)pyridine

Product 1

HCID 580762662-((4-(2-Nitroethyl)benzyl)oxy)pyridineYield 49%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dimethyl sulfoxide solution (150 mL) of acetic acid (7.4 mL) and 2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine (30.8 g, 120 mmol)) described in Manufacturing Example 1-2-3 was added sodium borohydride (2.45 g, 64.8 mmol) at 30° C. or lower. The reaction solution was stirred for 40 minutes at room temperature. Water, ethyl acetate, and diethyl ether were added at 30° C. or lower to the reaction solution, to separate the reaction solution into water and an organic layer. The aqueous layer was extracted with ethyl acetate. The previously obtained organic layer and the ethyl acetate layer obtained this time were combined, washed with water three times and saline once, dried over anhydrous magnesium sulfate, and filtered. This 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 (15.2 g).

Workup

  1. customto separate the reaction solution into water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. customThe previously obtained organic layer and the ethyl acetate layer obtained this time
  4. washwashed with water three times and saline once
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThis filtrate was concentrated under a reduced pressure
  8. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4)

Sources & evidence

ORD record
ord-cbb297e652e64f52a769d492642c6e78
Source dataset
uspto-grants-2013_08
Patent number
US08513287B2

Reaction notes

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