Sulfuric Acid → HCID 22729011, Verbindung

HRID 460600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460600
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].C([Li])CCC.[CH3:11][O:12][C:13]1[C:21]2[CH:20]=[C:19]([C:22](OC)=O)[O:18][C:17]=2[CH:16]=[CH:15][CH:14]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C1COCC1>[CH3:11][O:12][C:13]1[C:21]2[CH:20]=[C:19]([C:22]3[O:5][N:4]=[C:2]([CH3:3])[CH:1]=3)[O:18][C:17]=2[CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 5

HCID 1118Sulfuric AcidHCID 67180Acetone, oximeHCID 516892Sodium BicarbonateHCID 22729192Methyl 4-methoxybenzofuran-2-carboxylateHCID 178418339Butyllithium

Produkt 1

HCID 22729011HCID 22729011, VerbindungAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution (160 ml) of acetone oxime (5.0 g) in THF was added dropwise n-butyllithium (1.6 M hexane solution) over 15 min under ice-cooling and the mixture was stirred for 1 hr. Thereto was added dropwise a solution (60 ml) of methyl 4-methoxybenzo(b)furan-2-carboxylate (6.7 g) in THF and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into ice water, and conc. sulfuric acid (4 ml) was added carefully. The mixture was stirred for 20 min more. The aqueous layer was neutralized with sodium hydrogencarbonate and extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure to give the title compound (3.0 g) as yellow crystals.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. additionwas added carefully
  4. stirringThe mixture was stirred for 20 min more
  5. extractionextracted with ethyl acetate
  6. washAfter washing with water
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b79b9ab01cbc4b0092811f232f1a42cf
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196199B2

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