Acetic Acid → 2-Methyl-5-(4-(2-nitro-ethyl)-benzyl)-furan

HRID 77911Notes

Reaction equation

HRID 77911 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[N+:16]([O-:18])=[O:17])=[CH:10][CH:9]=2)=[CH:5][CH:6]=1.C(O)(=O)C.CS(C)=O.[BH4-].[Na+]>O>[CH3:1][C:2]1[O:3][C:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N+:16]([O-:18])=[O:17])=[CH:10][CH:9]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 592554362-Methyl-5-(4-((E)-2-nitro-vinyl)-benzyl)-furan

Product 1

HCID 592555272-Methyl-5-(4-(2-nitro-ethyl)-benzyl)-furanYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-methyl-5-(4-((E)-2-nitro-vinyl)-benzyl)-furan (120 mg) described in Manufacturing Example 46-1-4, acetic acid (0.2 mL) and dimethyl sulfoxide (3.4 mL) was added sodium borohydride (29 mg, 0.77 mmol) at room temperature while cooling appropriately, which was stirred for 20 minutes at room temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:5) to obtain the title compound (90 mg, 77%).

Workup

  1. temperaturewhile cooling appropriately
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. concentrationwas concentrated under a reduced pressure
  5. customThe residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:5)

Sources & evidence

ORD record
ord-cc8f2103f6094bcda53c8f1b31886271
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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