Triphenylphosphine → ethyl (2E,4E)-5-(2,6-dimethoxyphenyl)-2-[(triphenylphosphoranylidene)amino]penta-2,4-dienoate

HRID 1040330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040330
[N:1](/[C:4](=[CH:10]/[CH:11]=[CH:12]/[C:13]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=1[O:21][CH3:22])/[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-].[C:23]1([P:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH3:22][O:21][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([O:19][CH3:20])[C:13]=1/[CH:12]=[CH:11]/[CH:10]=[C:4](/[N:1]=[P:29]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)\[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 86637359Ethyl (2E,4E)-2-azido-5-(2,6-dimethoxyphenyl)penta-2,4-dienoate

Produkt 1

HCID 86637360ethyl (2E,4E)-5-(2,6-dimethoxyphenyl)-2-[(triphenylphosphoranylidene)amino]penta-2,4-dienoateAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Add, dropwise, a solution of 5 g of ethyl (2E,4E)-2-azido-5-(2,6-dimethoxyphenyl)penta-2,4-dienoate (16.5 mmol) in 60 mL of DCM to a solution of 4.37 g (16.7 mmol) of triphenylphosphine in 40 mL of DCM. Stir the reaction mixture for 2 h at RT, then concentrate under reduced pressure. Solidify the residue obtained in 100 mL of isopropyl ether, then filter on a frit and rinse with 50 mL of isopropyl ether, giving 7.9 g of ethyl (2E,4E)-5-(2,6-dimethoxyphenyl)-2-[(triphenylphosphoranylidene)amino]penta-2,4-dienoate in the form of a white solid.

Aufarbeitung

  1. additionAdd
  2. concentrationconcentrate under reduced pressure
  3. customobtained in 100 mL of isopropyl ether
  4. filtrationfilter on a frit
  5. washrinse with 50 mL of isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-73589baf8cef4b8a87b694d1a6815eb4
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552201B2

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