Hydrochloric Acid → {[5-(1-Methyl-1-hydroxyethyl)isoxazol-3-yl]methyl}malononitrile

HRID 2261354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261354
[OH:1][C:2]([C:5]1[O:9][N:8]=[C:7]([CH:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])[CH:6]=1)([CH3:4])[CH3:3].C[Mg]Br.Cl>O1CCOCC1.O1CCCC1.[Cu]I>[OH:1][C:2]([C:5]1[O:9][N:8]=[C:7]([CH2:10][CH:11]([C:12]#[N:13])[C:14]#[N:15])[CH:6]=1)([CH3:4])[CH3:3]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 57736335{[5-(1-Hydroxy-1-methylethyl)-isoxazol-3-yl]methylidene}malononitrileHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 57736354{[5-(1-Methyl-1-hydroxyethyl)isoxazol-3-yl]methyl}malononitrileAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1.02 g of {[5-(1-hydroxy-1-methylethyl)-isoxazol-3-yl]methylidene}malononitrile was dissolved in 50 ml of 1,4-dioxane. Thereto, 0.05 g of copper(I) iodide was added and 9 ml of a 1.4 M solution of methylmagnesium bromide in tetrahydrofuran was then added under ice-cooling. The mixture was stirred for 1 hour under ice-cooling. The reaction mixture was added to 0.1 M hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.53 g of {1-[5-(1-hydroxy-1-methylethyl)-isoxazol-3-yl]methyl}malononitrile.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f6d23a6a70414449a39f78a2186ea3f1
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846956B2

Notizen zur Reaktion

Wird geladen…