HCID 66755610, Verbindung → HCID 66756428, Verbindung

HRID 1643831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643831
[CH2:1]([C:4]1[C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[C:25]([O:27][CH3:28])=[O:26])[CH:2]=[CH2:3]>C(Cl)Cl.C(#N)C.[Pd](Cl)Cl>[CH3:24][S:21]([C:18]1[CH:17]=[CH:16][C:15]([O:14][C:13]2[C:4]([CH:1]=[CH:2][CH3:3])=[C:5]([C:25]([O:27][CH3:28])=[O:26])[CH:6]=[C:7]([CH:12]=2)[C:8]([O:10][CH3:11])=[O:9])=[CH:20][CH:19]=1)(=[O:22])=[O:23]

Komponenten

4

Edukt 1

HCID 66755610HCID 66755610, Verbindung

Produkt 1

HCID 66756428HCID 66756428, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11769946Acetonitrile palladium dichlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of dimethyl 4-allyl-5-(4-(methylsulfonyl)phenoxy)isophthalate (3.0 g, 8.814 mmol) in CH2Cl2 (25 mL) was added bis(acetonitrile-palladium(II) chloride (229 mg, 0.881 mmol). The mixture was refluxed under N2 for 14 hours. After removal of the solvent, the crude material was introduced into a silica gel column and eluted with EtOAc in hexanes (10/90 to 30/70) to afford the title compound (2.65 g, 88%) as a white solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.82 (dd, J=6.69, 1.79 Hz, 3 H) 3.04-3.18 (m, 3 H) 3.93 (d, 6 H) 6.00 (none, 1 H) 6.22 (dd, J=16.01, 6.78 Hz, 1 H) 6.62 (dd, J=16.01, 1.70 Hz, 1 H) 6.94-7.09 (m, 2 H) 7.77 (d, J=1.70 Hz, 1 H) 7.85-8.00 (m, 2 H) 8.28 (d, J=1.70 Hz, 1 H); LC-MS(ESI)+ m/z=405.00 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was refluxed under N2 for 14 hours
  2. customAfter removal of the solvent
  3. additionthe crude material was introduced into a silica gel column
  4. washeluted with EtOAc in hexanes (10/90 to 30/70)

Quellen und Nachweise

ORD-Eintrag
ord-75408cba25b145af9b8fcd46d4b4e26c
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119624B2

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