Potassium Hydroxide → 6-{[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}-1-benzothiophene-2-carboxylic acid

HRID 1172891Notes

Reaction equation

HRID 1172891 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([CH2:14][C:15]3[CH:28]=[CH:27][C:18]4[CH:19]=[C:20]([C:22]([O:24]CC)=[O:23])[S:21][C:17]=4[CH:16]=3)=[N:11][N:10]=2)=[CH:5][CH:4]=1.[OH-].[K+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][C:12]([CH2:14][C:15]3[CH:28]=[CH:27][C:18]4[CH:19]=[C:20]([C:22]([OH:24])=[O:23])[S:21][C:17]=4[CH:16]=3)=[N:11][N:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59424234Ethyl 6-{[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}-benzothiophene-2-carboxylate

Product 1

HCID 576245656-{[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}-1-benzothiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 6-{[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}-1-benzothiophene-2-carboxylate (70 mg, 0.18 mmol) in THF (2.5 mL) was treated with 1M KOH solution (0.89 mL, 0.89 mmol) and stirred at ambient temperature for 12 hours. The reaction was partitioned between 1M HCl and ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated to give the title compound as a white solid. LC/MS (EI): cal'd 367.0 (MH+), exp 367.0 (MH+).

Workup

  1. customThe reaction was partitioned between 1M HCl and ethyl acetate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-74f3594aad754130b3ee096d48674936
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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