Sodium borohydride → HCID 44481212, compound

HRID 452789Notes

Reaction equation

HRID 452789 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=4)[C:11]=3[CH:24]=2)=[N:4][N:3]=1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:16]=[CH:17][C:18]([CH:21]([OH:23])[CH3:22])=[CH:19][CH:20]=4)[C:11]=3[CH:24]=2)=[N:4][N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 44482023HCID 44482023, compound

Product 1

HCID 44481212HCID 44481212, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-[4-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]phenyl]ethanone (0.30 g, 0.94 mmol) in ethanol (3 mL) was added sodium borohydride (90%, 59 mg, 1.41 mmol) at 0° C., and the resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/2-1/3) and recrystallized from hexane/ethyl acetate to give the title compound (0.23 g, yield 76%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/2-1/3)
  8. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-e47665d72c4f4c14a4bde2c22338754f
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

Loading…