Acetic Anhydride → HCID 21478721, Verbindung

HRID 2292492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2292492
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:22])=[C:13]([CH2:15][C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O-:26])(=O)[CH3:24].[K+].C(OC(=O)C)(=O)C.[N:35](OCCC(C)C)=O>C1C=CC=CC=1>[C:23]([N:22]1[C:12]2[C:13](=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)[C:15]([C:16]([O:18][CH:19]([CH3:20])[CH3:21])=[O:17])=[N:35]1)(=[O:26])[CH3:24]

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 517044Potassium AcetateHCID 21478799HCID 21478799, Verbindung

Produkt 1

HCID 21478721HCID 21478721, VerbindungAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

To a solution of isopropyl 5-benzyloxy-2-aminophenylactate (13.2 g) in benzene (140 ml) were added potassium acetate (4.33 g) and then acetic anhydride (13.5 g) and the mixture was heated under reflux for 20 minutes. A solution of isopentyl nitrite (7.76 g) in benzene (30 ml) was added dropwise over 5 minutes under reflux and then refluxing was continued for further 3 hours. After allowing to cool to room temperature, insolubles were filtered off with Celite and concentrated under reduced pressure. The resulting residue (16.9 g) was purified by a silica gel column chromatography (hexane:ethyl acetate=9:1-4:1) to give the title compound (10.9 g).

Aufarbeitung

  1. temperatureunder reflux for 20 minutes
  2. temperatureunder reflux
  3. temperaturerefluxing
  4. filtrationinsolubles were filtered off with Celite
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue (16.9 g) was purified by a silica gel column chromatography (hexane:ethyl acetate=9:1-4:1)

Quellen und Nachweise

ORD-Eintrag
ord-0c4788772b7245fb9a6581769e132543
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05684003

Notizen zur Reaktion

Wird geladen…