Sodium Hydroxide → 2-(4-(5-Ethyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxyacetic acid

HRID 1798589Notes

Reaction equation

HRID 1798589 reaction equation
ClC(Cl)(Cl)C([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]([CH2:16][CH3:17])=[N:14][N:15]=2)=[CH:7][CH:6]=1)O.[OH-:20].[Na+].[O:22]1[CH2:27][CH2:26][O:25][CH2:24]C1>CO>[CH2:16]([C:13]1[O:12][C:11]([C:8]2[CH:7]=[CH:6][C:5]([CH:26]([O:25][CH3:24])[C:27]([OH:22])=[O:20])=[CH:10][CH:9]=2)=[N:15][N:14]=1)[CH3:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 58432111HCID 58432111, compound

Product 1

HCID 584320572-(4-(5-Ethyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxyacetic acidYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
55 °C

Procedure

To a solution of 2,2,2-trichloro-1-(4-(5-ethyl-1,3,4-oxadiazol-2-yl)phenyl)ethanol (2.0 g, 6.25 mmol) in anhydr 1,4-dioxane (12.5 mL) and anhydr MeOH (15 mL) was added a solution of NaOH (1.25 g, 31.3 mmol) in anhydr MeOH (15 mL). After stirring for 4 hrs at 55° C., the mixture was cooled to room temperature and concentrated in vacuo. The residue was neutralized with saturated aqueous NH4Cl, acidified carefully with 1 M HCl and extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated in vacuo. The residue was triturated with Et2O to give 2-(4-(5-ethyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxyacetic acid as an off-white solid (1.2 g, 73% yield).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-9c2019c178794bf0a382b51e1579b80f
Source dataset
uspto-grants-2013_01
Patent number
US08343970B2

Reaction notes

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