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N-Iodosuccinimide → (4-Iodo-3-methylisoxazol-5-yl)acetic acid methyl ester

HRID 922243
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 922243
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[O:4][N:3]=1.[I:12]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[I:12][C:6]1[C:2]([CH3:1])=[N:3][O:4][C:5]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 12366875Methyl 2-(3-methylisoxazol-5-yl)acetate

Produkt 1

HCID 66685715(4-Iodo-3-methylisoxazol-5-yl)acetic acid methyl esterAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a sealed tube fitted with magnetic stirrer was charged methyl (3-methyl-1,2-oxazol-5-yl)acetate (0.9 g, 5.8 mmol) and N-iodosuccinimide (2.61 g, 11.6 mmol) in 10 mL trifluoroacetic acid. The reaction mixture was heated at 65° C. for 3 h. The RM was quenched with NaHCO3 solution (25 mL) and extracted with ethyl acetate (30 mL). The organic layer was washed with water (30 mL) and saturated brine solution (30 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as brown solid (1.18 g, yield: 72.4%).

Aufarbeitung

  1. customTo a sealed tube fitted with magnetic stirrer
  2. customThe RM was quenched with NaHCO3 solution (25 mL)
  3. extractionextracted with ethyl acetate (30 mL)
  4. washThe organic layer was washed with water (30 mL) and saturated brine solution (30 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b802d6b9b7f54f6ba2613b59b6818ddd
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09278915B2

Notizen zur Reaktion

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