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

HRID 78284

Reaction equation

HRID 78284 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:19]=[CH:18][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][CH:7]=1)([O-:3])=[O:2].C(O)(=O)C.[B-].[Na+].O>CS(C)=O.C(OCC)C.C(OCC)(=O)C>[N+:1]([CH2:4][CH2:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][O: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

8

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 22959485VertellusHCID 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 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine described in Manufacturing Example 230-1-3 (30.8 g, 120 mmol) and acetic acid (7.4 mL) in dimethyl sulfoxide (150 mL) was added sodium borohydrate (2.45 g, 64.8 mmol) at 30° C. or below. The reaction solution was stirred for 40 minutes at room temperature. Water, ethyl acetate and diethyl ether were added to the reaction solution at 30° C. or below, which was partitioned into aqueous and organic layers. The aqueous layer was extracted with ethyl acetate. The previously obtained organic layer and the ethyl acetate layer were combined, washed with water (3 times) and aqueous sodium chloride (once), 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, 49%).

Workup

  1. customwhich was partitioned into aqueous and organic layers
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washwashed with water (3 times) and aqueous sodium chloride (once),
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4)

Sources & evidence

ORD record
ord-4629484faaaf4b1fa005f795d681f7d8
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Linked notes

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