Water → 3-[5-(2,3-Dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]-1-(2-thienyl)propan-1-one

HRID 452710Notes

Reaction equation

HRID 452710 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:14][C:13]([CH2:15][CH2:16][C:17](N(OC)C)=[O:18])=[N:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[Mg]Br.O1CCCC1.[Cl-].[NH4+].O>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:14][C:13]([CH2:15][CH2:16][C:17]([C:24]4[S:23][CH:27]=[CH:26][CH:25]=4)=[O:18])=[N:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 866400353-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]-N-methoxy-N-methylpropionamideHCID 178420627HCID 178420627, compound

Product 1

HCID 686644033-[5-(2,3-Dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]-1-(2-thienyl)propan-1-oneYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]-N-methoxy-N-methylpropionamide (2.50 g, 8.24 mmol) in tetrahydrofuran (50 mL) was added 1 M (2-thienyl)magnesium bromide-tetrahydrofuran solution (9.9 mL, 9.9 mmol), and the resulting mixture was stirred at room temperature for 1 hr. A saturated aqueous ammonium chloride solution (50 mL) and water were added to the reaction mixture, 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 recrystallized from hexane/ethyl acetate to give the title compound (1.10 g, yield 41%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-75c8dd417cb54a658f60b781a781584e
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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