1-Methoxybuta-1,3-diene → 4-{2-[(e)-2-Methoxyethenyl]-2,3-dihydro-1-benzofuran-5-yl}benzonitrile

HRID 1064710

Reaktionsgleichung

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1I.[CH3:17][O:18][CH:19]=[CH:20][CH:21]=[CH2:22].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(Cl)Cl.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:17][O:18]/[CH:19]=[CH:20]/[CH:21]1[CH2:22][C:3]2[CH:4]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=3)[CH:6]=[CH:7][C:2]=2[O:1]1

Komponenten

Reaktionsbedingungen

Temperatur: 23 °C

Versuchsvorschrift

A solution of Example 1A (0.20 g, 0.623 mmol), 1-methoxybutadiene (0.18 g, 2.18 mmol), palladium diacetate (0.007 g, 0.031 mmol), sodium bicarbonate (0.261 g, 3.11 mmol) and tetrabutyl ammonium chloride (0.173 g, 0.623 mmol) was heated at 60° C. in DMF (3 mL) under an atmosphere of nitrogen for 36 hours. The reaction was cooled to 23° C., diluted with CH2Cl2 (50 mL), filtered through Celite. The solution was concentrated under reduce pressure and the residue was purified on silica using CH2Cl2 to give the titled compound (0.95 g, 55%). 1H NMR (CDCl3): 3.05 (m, 1H), 3.40 (m, 1H), 3.60 (s, 3H), 5.00 (m, 1H), 5.22 (m, 1H), 6.72 (d, J=14 Hz, 1H), 6.83 (d, J=7 Hz, 1H), 7.38 (m, 2H), 7.65 (m, 4H); MS (DCI): 278 (M+H+), 295 (M+NH4+).

Aufarbeitung

filtrationfiltered through Celite
concentrationThe solution was concentrated
customthe residue was purified on silica

Quellen und Nachweise

ORD-Eintrag: ord-dc0a3a54a55d49d59e592bf06816222b
Quelldatensatz: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06969730B2

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