Acetic Acid → HCID 59556865, compound

HRID 1173735Notes

Reaction equation

HRID 1173735 reaction equation
[CH2:1]([CH:8]1[C:12]([OH:13])=[CH:11][C:10](=[O:14])[N:9]1[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([Cl:23])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[BH4-].[Na+].O>C(#N)C>[CH2:1]([C@H:8]1[C@@H:12]([OH:13])[CH2:11][C:10](=[O:14])[N:9]1[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([Cl:23])[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 59557022HCID 59557022, compound

Product 1

HCID 59556865HCID 59556865, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-(2-benzyl-3-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-2-chlorobenzonitrile (400 mg) and acetic acid (0.60 mL) in acetonitrile (20 mL) was added sodium borohydride (86 mg) at 0° C. in small portions. The mixture was warmed to room temperature, and stirred for 3 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 tetrahydrofuran-hexane to give the title compound as colorless crystals (yield: 310 mg, 77%).

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 tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-9bb32241eeb742f7a81ac4d0f5dda523
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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