N-Iodosuccinimide → Ethyl 4-iodo-5-phenylisoxazole-3-carboxylate

HRID 1948457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948457
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:17]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[I:17][C:8]1[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:10][O:11][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 571142Ethyl 5-phenylisoxazole-3-carboxylate

Produkt 1

HCID 58537206Ethyl 4-iodo-5-phenylisoxazole-3-carboxylateAusbeute 152,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Large Scale: A mixture of ethyl 5-phenylisoxazole-3-carboxylate (3.05 g, 14.0 mmol) and N-iodosuccinimide (3.79 g, 16 9 mmol) in trifluoroacetic acid (78 mL) was stirred at room temperature for 3.5 h. The volatiles were removed under reduced pressure, and the residue was partitioned between ethyl acetate (150 mL) and water (150 mL). The organic layer was washed with a 1N aqueous solution of sodium hydroxide (150 mL), washed with a 3% aqueous solution of sodium bisulfate (2×150 mL), washed with brine (150 mL), and dried over anhydrous magnesium sulfate. Concentration under reduced pressure afforded ethyl 4-iodo-5-phenylisoxazole-3-carboxylate (4.69 g, 13.7 mmol, 97% yield) as a light yellow oil.

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (150 mL) and water (150 mL)
  3. washThe organic layer was washed with a 1N aqueous solution of sodium hydroxide (150 mL)
  4. washwashed with a 3% aqueous solution of sodium bisulfate (2×150 mL)
  5. washwashed with brine (150 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationConcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-435c688f03644f3c828025655b39809e
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399451B2

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