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

HRID 1891780Notes

Reaction equation

HRID 1891780 reaction equation
CS(C)=O.[CH3:5][C:6]1[CH:22]=[CH:21][C:9]([CH2:10][C:11]2[S:12][C:13](/[CH:16]=[CH:17]/[N+:18]([O-:20])=[O:19])=[CH:14][CH:15]=2)=[CH:8][CH:7]=1.C(O)(=O)C.[BH4-].[Na+]>O>[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][C:11]2[S:12][C:13]([CH2:16][CH2:17][N+:18]([O-:20])=[O:19])=[CH:14][CH:15]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 592553182-(4-Methyl-benzyl)-5-((E)-2-nitro-vinyl)-thiophene

Product 1

HCID 592554602-(4-Methyl-benzyl)-5-(2-nitro-ethyl)-thiopheneYield 43.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethyl sulfoxide (20.0 mL) solution of 2-(4-methyl-benzyl)-5-((E)-2-nitro-vinyl)-thiophene (1.20 g, 4.63 mmol) described in Manufacturing Example 92-1-3 and acetic acid (1.20 mL) was added sodium borohydride (280 mg, 7.41 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 20 minutes at room temperature. Water was then added dropwise at room temperature while cooling appropriately. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was crystallized with a tetrahydrofuran-ethyl acetate-heptane system and filtered to obtain the title compound (525 mg, 43.4%).

Workup

  1. temperaturewhile cooling appropriately under nitrogen atmosphere
  2. temperaturewhile cooling appropriately
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was crystallized with a tetrahydrofuran-ethyl acetate-heptane system
  9. filtrationfiltered

Sources & evidence

ORD record
ord-dd275baca03f415eaa1232ce335d8b3d
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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