Dimethylformamide → Methyl 7-cyano-2,3-dihydro-1-benzoxepine-4-carboxylate

HRID 2228301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2228301
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.[CH3:17][N:18](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:17]([C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1)#[N:18]

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 22990005Methyl 7-bromo-2,3-dihydro-1-benzooxepine-4-carboxylate

Produkt 1

HCID 18472647Methyl 7-cyano-2,3-dihydro-1-benzoxepine-4-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of methyl 7-bromo-2,3-dihydro-1-benzoxepine-4-carboxylate (1416 mg, 5.00 mmol), zinc cyanide (352 mg, 3. 00 mmol), tetrakis(triphenylphosphine)-palladium (347 mg, 0.30 mmol) and DMF(10 ml) was stirred at 80° C. for 3 hours. The mixture was concentrated under reduced pressure, and to the residue was added ethyl acetate. Insoluble materials were filtered off, which were washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The resulting crude product was recrystallized from ethyl acetate to give methyl 7-cyano-2,3-dihydro-1-benzoxepine-4-carboxylate (800 mg, 3.49 mmol, 70%). IR (KBr): 2222, 1721 cm−1.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionto the residue was added ethyl acetate
  3. filtrationInsoluble materials were filtered off
  4. washwhich were washed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting crude product was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-886a025cb6044477a043eb41249a4edc
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06413947B1

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