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

HRID 566115Notizen

Reaktionsgleichung

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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=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

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-6cdf39161f0641cfb7401f700c3e94c0
Quelldatensatz: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06172061B2

Notizen zur Reaktion

Wird geladen…