Tetrahydrofuran → 2-(7-Methoxynaphthalen-1-yl)acetonitrile

HRID 572698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572698
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]([NH2:16])=O)=[CH:5][CH:4]=1.C1COCC1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]#[N:16])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 9845Trifluoroacetic anhydrideHCID 151491272-(7-Methoxynaphthalen-1-yl)acetamide

Produkt 1

HCID 112640682-(7-Methoxynaphthalen-1-yl)acetonitrileAusbeute 101,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

30 g 7-methoxy-1-naphthaleneacetamide, 120 ml THF and 35.7 g triethylamine were added into reaction flask. The mixture was stirred and cooled with external ice saline bath. Trifluoroacetic anhydride was slowly added in drops. After completion of addition, it was stirred for further 15 min. Then, the ice bath was removed and stirring was carried out for 2 h at room temperature. After completion of the reaction, the reaction solution was evaporated. Subsequently, 200 ml water was added and the solution was filtered and dried after stirring for 0.5 hours, to obtain 28 g crude product. Recrystallization was carried out using 280 ml isopropyl ether and 1.4 g activated carbon to obtain 22 g refined product with the mp of 82-84° C. The yield is 80%.

Aufarbeitung

  1. temperaturecooled with external ice
  2. additionAfter completion of addition, it
  3. stirringwas stirred for further 15 min
  4. customThen, the ice bath was removed
  5. stirringstirring
  6. customAfter completion of the reaction
  7. customthe reaction solution was evaporated
  8. additionSubsequently, 200 ml water was added
  9. filtrationthe solution was filtered
  10. customdried
  11. stirringafter stirring for 0.5 hours

Quellen und Nachweise

ORD-Eintrag
ord-113758f9cfd74f74a0d617ade4459445
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029420B2

Notizen zur Reaktion

Wird geladen…