Potassium tert-butoxide → 2-(Methoxymethyl)-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole

HRID 452819Notes

Reaction equation

HRID 452819 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH:14]=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=4)[C:12]=3[CH:27]=2)=[N:6][N:7]=1.C[C:29](C)([O-:31])C.[K+]>CO>[CH3:29][O:31][CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH:14]=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=4)[C:12]=3[CH:27]=2)=[N:6][N:7]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxide2×HCID 68663800HCID 68663800, compound

Product 1

HCID 686643802-(Methoxymethyl)-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazoleYield 67.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-(chloromethyl)-5-[3-[3-(trifluoromethoxy)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole (0.30 g, 0.76 mmol) and potassium tert-butoxide (85%, 0.12 g, 0.91 mmol) in methanol (5 mL) was stirred overnight at room temperature. Potassium tert-butoxide (85%, 0.03 g, 0.23 mmol) was added to the reaction mixture, and the resulting mixture was stirred at 50° C. overnight. The reaction mixture was concentrated under reduced pressure, saturated aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) and recrystallized from hexane/ethyl acetate to give the title compound (0.20 g, yield 67%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous ammonium chloride solution
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)
  8. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-11c5b0a72dec4d949a765b2a3b71fa86
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

Loading…