Acetic Acid → HCID 59255516, compound

HRID 78031Notes

Reaction equation

HRID 78031 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 59255516HCID 59255516, compoundYield 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-c725aad2e68b4112b43eeaf2fa241e23
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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