Potassium Carbonate → HCID 44590414, compound

HRID 452705Notes

Reaction equation

HRID 452705 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:12](S(C)(=O)=O)=[N:13][N:14]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][OH:30]>CN(C)C=O.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:12]([O:30][CH2:29][C:28]4[CH:31]=[CH:32][CH:33]=[C:26]([F:25])[CH:27]=4)=[N:13][N:14]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680083-Fluorobenzylic alcoholHCID 68663351HCID 68663351, compound

Product 1

HCID 44590414HCID 44590414, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2,3-dihydro-1-benzofuran-5-yl)-5-(methylsulfonyl)-1,3,4-oxadiazole (0.15 g, 0.56 mmol), potassium carbonate (111 mg, 0.80 mmol) and 3-fluorobenzyl alcohol (91 μL, 0.83 mmol) in N,N-dimethylformamide (5 mL) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=3/1) and recrystallized from hexane/ethyl acetate to give the title compound (84 mg, yield 48%) as colorless crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=3/1)
  5. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-e6ef115e7b4f4184b1340cef309c4b4e
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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