Acetic Acid → HCID 59255299, compound

HRID 78038Notes

Reaction equation

HRID 78038 reaction equation
O1CCCC1.CS(C)=O.[O:10]1[CH2:14][CH2:13][CH2:12][CH: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[CH2:14][CH2:13][CH2:12][CH: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 59255150HCID 59255150, compound

Product 1

HCID 59255299HCID 59255299, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed tetrahydrofuran-dimethyl sulfoxide (1:1, 10 mL) solution of 4-(2-(tetrahydrofuran-2-yl)-ethyl)-((E)-2-nitro-vinyl)-benzene (646 mg, 2.61 mmol) described in Manufacturing Example 82-1-4 and acetic acid (0.6 mL) was added sodium borohydride (148 mg, 3.92 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 10 minutes at room temperature. Water was added dropwise into the reaction mixture 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 (ethyl acetate:heptane=2:8) to obtain the title compound (421 mg, 65%).

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 (ethyl acetate:heptane=2:8)

Sources & evidence

ORD record
ord-8b7f1aed98704dfea8d0a6f10c872911
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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