Acetic Acid → HCID 59556928, compound

HRID 1967409Notes

Reaction equation

HRID 1967409 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C:14](=[O:15])[CH:13]=[C:12]([OH:16])[CH:11]2[CH:17]([CH3:19])[CH3:18])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(O)(=O)C.[BH4-].[Na+].O>C(#N)C>[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C:14](=[O:15])[CH2:13][C@H:12]([OH:16])[C@@H:11]2[CH:17]([CH3:19])[CH3:18])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 59556864HCID 59556864, compound

Product 1

HCID 59556928HCID 59556928, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-chloro-4-[3-hydroxy-2-(1-methylethyl)-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]benzonitrile (300 mg) and acetic acid (0.68 mL) in acetonitrile (10 mL) was added sodium borohydride (103 mg) at 0° C. in small portions. The mixture was warmed to room temperature and stirred for 1 hr. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluent: hexane:ethyl acetate=4:1→-ethyl acetate), and recrystallized from hexane-ethyl acetate to give the title compound as colorless crystals (yield: 76 mg, 25%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (eluent: hexane:ethyl acetate=4:1→-ethyl acetate)
  6. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-c6f3567ba16142b5a8f9f9f83ebae5d5
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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