Triphenylphosphine → HCID 86671497, Verbindung

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Reaktionsgleichung

Br[C:2]1[C:3]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[CH3:15])=[CH:4][S:5][CH:6]=1.C(P(=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=O)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:43]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:11]([C:10]1[CH:13]=[CH:14][C:7]([C:3]2[C:2](/[CH:43]=[CH:37]/[C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:6][S:5][CH:4]=2)=[C:8]([CH3:15])[CH:9]=1)#[N:12]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To a solution of 4-(4-bromothiophen-3-yl)-3-methylbenzonitrile (2.4 g, 8.7 mmol) and ethyl 2-(tritylphosphinylidene)acetate (2.6 g, 26 mmol) in DMF (10 mL) was added Pd(OAc)2 (194 mg, 0.87 mmol) and PPh3 (228 mg, 0.87 mmol), and the mixture was stirred at 150° C. under nitrogen overnight. The mixture was diluted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, concentrated in vacuo, and purified on silica gel column (PE: EtOAc=20:1) to give (E)-ethyl 3-(4-(4-cyano-2-methylphenyl)thiophen-3-yl)acrylate (Scheme III, 14, X1=4-cyano-2-methylphenyl) (1 g, yield 39%) as yellow oil. 1H NMR (CD3OD 400 MHz): δ 8.03 (d, J=2.8 Hz, 1H), 7.71 (s, 1H), 7.64 (d, J=7.6 Hz, 1H), 7.39-7.34 (m, 2H), 7.28 (d, J=16 Hz, 1H), 6.06 (d, J=16.4 Hz, 1H), 4.15 (q, J=7.2 Hz, 2H), 2.15 (s, 3H), 1.24 (t, J=7.2 Hz, 3H).

Aufarbeitung

washThe organic layer was washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
custompurified on silica gel column (PE: EtOAc=20:1)

Quellen und Nachweise

ORD-Eintrag: ord-dafe27e2f16b4c2d8ef05ebd4f0f3276
Quelldatensatz: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08586624B2

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