Dimethylformamide → 6-(Cyclopropylmethoxy)-1,3-benzoxazole

HRID 1026202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026202
[O:1]1[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[CH2:12][CH:13]1[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH:13]1([CH2:12][O:10][C:7]2[CH:8]=[CH:9][C:4]3[N:3]=[CH:2][O:1][C:5]=3[CH:6]=2)[CH2:15][CH2:14]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 116939151,3-Benzoxazol-6-ol

Produkt 1

HCID 677784246-(Cyclopropylmethoxy)-1,3-benzoxazoleAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 1,3-benzoxazol-6-ol (2.31 g), (bromomethyl)cyclopropane (3.46 g), potassium carbonate (3.54 g) and DMF (25 mL) was stirred at 60° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.88 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-36dfa2f838c5406e9edd060f48e0a5ba
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729102B2

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