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

HRID 25835

Reaction equation

HRID 25835 reaction equation
[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

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 121347052-(3-Isobutyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 12134712Trifluoro-methanesulfonic acid 3-benzyl-4'-(2-Cyano-ethyl)-2'-isobutyl-biphenyl-4-yl ester

Product 1

HCID 225652423-(3'-Benzyl-2,3''-diisobutyl-4''-methoxy-1,1':4',1''-terphenyl-4-yl)propanenitrileYield 88.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 20074477Dimethoxyethane ethanolSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  1. concentrationAfter concentrating the mixture in vacuo the residue
  2. extractionextracted with CH2Cl2
  3. dry with materialfractions were dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-31d64c265f054602925d4a1b6b027bbd
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Linked notes

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