Acetic Acid → 4-(2-Furan-2-yl-ethyl)-(2-nitro-ethyl)-benzene

HRID 1891747Notes

Reaction equation

HRID 1891747 reaction equation
O1CCCC1.CS(C)=O.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[N+:25]([O-:27])=[O:26])=[CH:19][CH:18]=1.C(O)(=O)C.[BH4-].[Na+]>O>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][N+:25]([O-:27])=[O:26])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 21830753dimethylsulfoxide THFHCID 59255163HCID 59255163, compound

Product 1

HCID 592555164-(2-Furan-2-yl-ethyl)-(2-nitro-ethyl)-benzeneYield 53.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed tetrahydrofuran-dimethyl sulfoxide (1:1, 10 mL) solution of 4-(2-furan-2-yl-ethyl)-((E)-2-nitro-vinyl)-benzene (554 mg, 2.28 mmol) described in Manufacturing Example 80-1-5 and acetic acid (0.5 mL) was added sodium borohydride (129 mg, 3.42 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 10 minutes at room temperature. Water was added dropwise into this reaction solution at room temperature while cooling appropriately. The reaction mixture was partitioned into water and ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (t-butylmethyl ether:heptane=5:95) to obtain the title compound (300 mg, 53%).

Workup

  1. temperaturewhile cooling appropriately under nitrogen atmosphere
  2. temperaturewhile cooling appropriately
  3. customThe reaction mixture was partitioned into water and ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (t-butylmethyl ether:heptane=5:95)

Sources & evidence

ORD record
ord-f321fe4499f843188a0a92dcc8bf5356
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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