Sodium Carbonate → 4-(Benzo[b]thiophen-5-yl)-3,5-dimethylisoxazole

HRID 1009003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009003
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[CH3:11][C:12]1[C:16](C(B(O)O)=O)=[C:15]([CH3:22])[O:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C>[S:9]1[CH:8]=[CH:7][C:6]2[CH:10]=[C:2]([C:16]3[C:12]([CH3:11])=[N:13][O:14][C:15]=3[CH3:22])[CH:3]=[CH:4][C:5]1=2

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27765785-Bromo-1-benzothiopheneHCID 673054143,5-Dimethyl-4-isoxazoylboronic acid

Produkt 1

HCID 534868054-(Benzo[b]thiophen-5-yl)-3,5-dimethylisoxazoleAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5-bromo-1-benzothiophene (ABCR, CAS: 133150-64-8, 1.0 6 g, 5.0 mmol) in dimethoxyethane (60 mL) and ethanol (6.0 mL) was added 3,5-dimethyl-4-isoxazoylboronic acid (1.0 g, 7.5 mmol), and 2 m sodium carbonate (2.0 mL). The reaction mixture was degassed 2-3 times, tetrakis-(triphenylphosphine)palladium (0.813 g, 0.7 mmol) was added, and the mixture was stirred for 6 h at 80° C. and concentrated. The residue was taken up in water and extracted with ethyl acetate. The organics were washed, dried and concentrated. The crude product was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain 4-benzo[b]thiophen-5-yl-3,5-dimethyl-isoxazole (0.69 g) as a light yellow solid. MS (ISP): m/e 230.1 (M+H)+

Aufarbeitung

  1. additionwas added
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-38a7e0a2adcd4b80ab7c45ce2197dfc2
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973051B2

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