Hydrochloric Acid → 3-[5-(2,3-Dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionic acid

HRID 452708Notes

Reaction equation

HRID 452708 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]([O:19]CC)=[O:18])=[N:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.C(O)C.[OH-].[Na+].Cl>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]([OH:19])=[O:18])=[N:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 68664485Ethyl 3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionate

Product 1

HCID 621995883-[5-(2,3-Dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionic acidYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionate (5.20 g, 18.04 mmol), ethanol (30 mL) and tetrahydrofuran (15 mL) was added 1 M aqueous sodium hydroxide solution (20 mL), and the resulting mixture was stirred at room temperature for 3 hr. The reaction mixture was neutralized with 5 M hydrochloric acid, and extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from methanol/diethyl ether to give the title compound (3.63 g, yield 77%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate/tetrahydrofuran
  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 methanol/diethyl ether

Sources & evidence

ORD record
ord-b8bc09423db5404d90ba1d9f9332090c
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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