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

HRID 2359180Notes

Reaction equation

HRID 2359180 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-babb227088cf4bdba0d28749c5e2067c
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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