4-Isobutylbenzoic acid → {3-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]phenyl}methanol

HRID 2242246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2242246
C(C1NC=CN=1)(C1NC=CN=1)=O.[CH2:13]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=1)[CH:14]([CH3:16])[CH3:15].O[N:27]=[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][OH:37])[CH:31]=1)[NH2:29].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O.C1COCC1.[Cl-].[Na+].O.CN(C=O)C>[CH2:13]([C:17]1[CH:18]=[CH:19][C:20]([C:21]2[O:23][N:29]=[C:28]([C:30]3[CH:31]=[C:32]([CH2:36][OH:37])[CH:33]=[CH:34][CH:35]=3)[N:27]=2)=[CH:24][CH:25]=1)[CH:14]([CH3:15])[CH3:16]

Komponenten

9

Edukt 4

HCID 381114-Isobutylbenzoic acidHCID 2724141Tetrabutylammonium FluorideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 74865044N'-hydroxy-3-(hydroxymethyl)benzimidamide

Produkt 1

HCID 59204314{3-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]phenyl}methanolAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Carbonyl diimidazole (421 mg, 2.60 mmol) was added to a solution of 4-isobutyl benzoic acid (386 mg, 2.17 mmol) and DMF (10 mL) and stirred for 2 hours at room temperature. N′-hydroxy-3-(hydroxymethyl)benzenecarboximidamide (360 mg, 2.17 mmol) was added to the reaction mixture and stirred for 18 hours at ambient temperature. The reaction was diluted with water and extracted with ethyl acetate (2×) and the combined organic extracts were washed with 0.25 N sodium hydroxide, water and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give a crude residue. The crude residue was dissolved in THF (6 mL) and treated with tetrabutyl ammonium fluoride (1M in THF, 2.4 mL, 2.38 mmol). The solution was stirred at ambient temperature for 18 hours, diluted with brine and extracted with ethyl acetate. The combined organic layers were concentrated in vacuo. Purification by flash chromatography (silica, 1:9 to 2:3 EtOAc:hexanes) provided the title compound (193 mg, 29% yield) as a solid.

Aufarbeitung

  1. stirringstirred for 18 hours at ambient temperature
  2. extractionextracted with ethyl acetate (2×)
  3. washthe combined organic extracts were washed with 0.25 N sodium hydroxide, water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude residue
  8. stirringThe solution was stirred at ambient temperature for 18 hours
  9. extractionextracted with ethyl acetate
  10. concentrationThe combined organic layers were concentrated in vacuo
  11. customPurification by flash chromatography (silica, 1:9 to 2:3 EtOAc:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8e7bb46ba6ce4e1c98ccb924ef45f340
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07671043B2

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