Sodium Carbonate → 3-(3'-Benzyl-2,3''-diisobutyl-4''-methoxy-1,1':4',1''-terphenyl-4-yl)propanenitrile

HRID 971348

Reaktionsgleichung

[CH2:1]([C:8]1[CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]#[N:31])=[CH:24][C:23]=2[CH2:32][CH:33]([CH3:35])[CH3:34])[CH:11]=[CH:12][C:13]=1OS(C(F)(F)F)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:36]([C:40]1[CH:41]=[C:42](B2OC(C)(C)C(C)(C)O2)[CH:43]=[CH:44][C:45]=1[O:46][CH3:47])[CH:37]([CH3:39])[CH3:38].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.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>[CH2:1]([C:8]1[CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]#[N:31])=[CH:24][C:23]=2[CH2:32][CH:33]([CH3:35])[CH3:34])[CH:11]=[CH:12][C:13]=1[C:42]1[CH:43]=[CH:44][C:45]([O:46][CH3:47])=[C:40]([CH2:36][CH:37]([CH3:38])[CH3:39])[CH:41]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

134.6 mg (0.27 mmol) Trifluoro-methanesulfonic acid 3-benzyl-4′-(2-Cyano-ethyl)-2′-isobutyl-biphenyl-4-yl ester (54), 96.9 mg (0.33 mmol, 1.24 eq.) 2-(3-isobutyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (11) and 46.7 mg (40 μmol, 0.15 eq.) Pd(Ph3P)4 were dissolved in 7 ml DME/EtOH (9+1). To this yellow solution 0.27 ml (0.54 mmol, 2.00 eq.) of a 2 M aq. Na2CO3-solution was added and the resulting mixture was heated at 80° C. for 19 h. After concentrating the mixture in vacuo the residue was taken up in water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Column chromatography (hexanes/EtOAc (6+1)) yielded 122.9 mg (0.24 mmol, 88.26%) 3-(3′-Benzyl-2,3″-diisobutyl-4″-methoxy-1,1′:4′,1″-terphenyl-4-yl)propanenitrile (55) as a clear oil. Rf (hexanes/EtOAc (6+1))=0.20. 1H-NMR (500 MHz, CDCl3): δ=0.69 (d, 6H, J=6.62 Hz, 2*CH3), 0.84 (d, 6H, J=6.62 Hz, 2*CH3), 1.63 (m, 1H, CH), 1.83 (m, 1H, CH), 2.42 (d, 2H, J=7.25 Hz, CH2), 2.44 (d, 2H, J=7.25 Hz, CH2), 2.61 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.93 (t, 2H, J=7.41 Hz, CH2CH2CN), 3.81 (s, 3H, OCH3), 3.98 (s, 2H, CH2Ph), 6.81 (d, 1H, J=8.51 Hz), 6.96 (m, 2H), 7.00-7.18 (m, 10H), 7.24-7.26 (d, 1H, J=7.57 Hz). MS (EI): m/z=517 (10), 516 (45), 515 (100), 472 (10), 381 (8), 91 (20). HR-MS (EI): Calcd. for C37H41NO: 515.318814. Found: 515.319235.

Aufarbeitung

concentrationAfter concentrating the mixture in vacuo the residue
extractionextracted with CH2Cl2
dry with materialfractions were dried over MgSO4
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-9dab3958f75049a0a329ee4e9d676014
Quelldatensatz: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07312246B2

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