Water → 3-(3'-Benzyl-4''-hydroxy-2,3''-diisobutyl-1,1':4',1''-terphenyl-4-yl)propanenitrile

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

0.71 ml (0.71 mmol, 2.98 eq.) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 122.8 mg (0.238 mmol) 3-(3′-Benzyl-2,3″-diisobutyl-4″-methoxy-1,1′:4′,1″-terphenyl-4-yl)propanenitrile (55) in 5 ml dry CH2Cl2 at 0° C. via syringe. After that the solution was stirred for 90 min at 0° C. and then for 5 h at r.t. The reaction mixture was then added to water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Column chromatography (hexanes/EtOAc (2+1)) yielded 119.3 mg (0.24 mmol, 99.91%) 3-(3′-Benzyl-4″-hydroxy-2,3″-diisobutyl-1,1′:4′,1″-terphenyl-4-yl)propanenitrile (56) as a colorless oil. Rf (hexanes/EtOAc (2+1))=0.40. 1H-NMR (500 MHz, CDCl3): δ=0.69 (d, 6H, J=6.62 Hz, 2*CH3), 0.86 (d, 6H, J=6.62 Hz, 2*CH3), 1.63 (m, 1H, CH), 1.87 (m, 1H, CH), 2.43 (d, 2H, J=7.25 Hz, CH2), 2.47 (d, 2H, J=7.09 Hz, CH2), 2.61 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.93 (t, 2H, J=7.41 Hz, CH2CH2CN), 3.95 (s, 2H, CH2Ph), 5.51 (s, 1H, OH), 6.88 (d, 1H, J=2.05 Hz), 6.95 (m, 2H), 6.97-7.26 (m, 11H). MS (EI): m/z=502 (40), 501 (100), 458 (4), 367 (10), 327 (7), 307 (8), 263 (8), 91 (43). HR-MS (EI): Calcd. for C36H39NO: 501.303164. Found: 501.303902.

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