Triphenylphosphine → HCID 21263166, Verbindung

HRID 567883Notizen

Reaktionsgleichung

Br[C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:15]=[C:14](OC)[CH:13]=[C:12]([O:18]C)[C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1.[C:22]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:23]=1.C(N(C(C)C)CC)(C)C>CN1CCCC1=O.C(OCC)(=O)C.[Cu](I)I>[CH2:22]([C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[C:12]([OH:18])[C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1)[CH3:23]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

2-Bromo-7,9-dimethoxy-10,11-dihydrodibenz[b,f]oxepin-10-one 500 mg (F. W. 349.18, 1.43 mmol) prepared in the first stage of Production Example 79, triphenylphosphine 75 mg (F. W. 262.29, 0.062 mmol), trisbenzyldene acetone dipalladium chloroform complex 74 mg (F. W. 1035.08, 0.015 mmol), diisopropylethylamine 575 μl (F. W. 98.22, d=0.742, 2.86 mmol), ethynyl trimethylsillane 350 μl (F. W. 98.22, d=0.742, 2.86 mmol) and copper iodide 27.5 mg (F. W. 190.44, 0.143 mmol) were dissolved in N-methyl-2-pyrrolidone (5 ml) and, after substituting with argon atmosphere, they were stirred with heating at 80° C. for one hour. The reaction mixture was diluted with ethyl acetate and washed with water and saturated sodium chloride solution. The organic layer was dried and concentrated and the resulting residue was purified by a silica gel column chromatography to give the title compound 420 mg (F. W. 367.419, 66%). The peaks of this compound in 1H-NMR (400 MHz, CDCl3) were as follows.

Aufarbeitung

washwashed with water and saturated sodium chloride solution
customThe organic layer was dried
concentrationconcentrated
customthe resulting residue was purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-6d299c3be5b34cc293512871c358c2e4
Quelldatensatz: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06180659B2

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