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

HRID 1891518Notes

Reaction equation

HRID 1891518 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 dimethylsulfoxide (150 mL) solution of acetic acid (7.4 mL) and 2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine (30.8 g, 120 mmol) described in Manufacturing Example 2-2-3 was added sodium borohydride (2.45 g, 64.8 mmol) at 30° C. or less. The reaction solution was stirred at room temperature for 40 minutes. To the reaction solution were added water, ethyl acetate and diethyl ether at 30° C. or less to partition it into water and an organic layer. The water layer was extracted with ethyl acetate. This ethyl acetate layer was combined with the organic layer obtained previously, washed with water (3 times) and aqueous sodium chloride (1 time), dried over anhydrous magnesium sulfate, and then filtered. The 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 partition it into water
  2. extractionThe water layer was extracted with ethyl acetate
  3. customobtained previously
  4. washwashed with water (3 times) and aqueous sodium chloride (1 time)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe 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-6824c40d63314e9d92a4de72df500092
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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