Benzaldehyde, 4-(diphenylamino)- → (E)-N,N-diphenyl-4-(4-(triphenylen-2-yl)styryl)aniline

HRID 871822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871822
[CH:1]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[C:19]1[CH:33]=[CH:32][C:22]([CH2:23]P(=O)(OCC)OCC)=[CH:21][CH:20]=1.[C:34]1([N:40]([C:47]2[CH:54]=[CH:53][C:50]([CH:51]=O)=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CC(C)([O-])C.[K+]>C1COCC1>[C:34]1([N:40]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:47]2[CH:54]=[CH:53][C:50](/[CH:51]=[CH:23]/[C:22]3[CH:32]=[CH:33][C:19]([C:2]4[CH:3]=[CH:4][C:5]5[C:6]6[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=6)[C:12]6[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=6)[C:18]=5[CH:1]=4)=[CH:20][CH:21]=3)=[CH:49][CH:48]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Komponenten

5

Edukt 3

HCID 77846Benzaldehyde, 4-(diphenylamino)-HCID 23665647Potassium tert-butoxideHCID 86675394Diethyl 4-(triphenylen-2-yl)benzylphosphonate

Produkt 1

HCID 86675396(E)-N,N-diphenyl-4-(4-(triphenylen-2-yl)styryl)anilineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Compound E (1.0 g, 2.20 mmol) or E1 and 4-(N,N-diphenylamino)benzaldehyde (0.72 g, 2.64 mmol) and dry THF (20 ml) were charged in two necked-bottle in an ice bath, potassium-tert-butoxide (0.49 g, 4.4 mmol) in dry THF (20 ml) was added under nitrogen. The reaction mixture was stirred for 15 min at 0° C., followed by 1 h at room temperature. The solution mixture was extracted with ethyl acetate and washed with water. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure to afford a crude product that was purified by sublimating at a temperature of 260° C. to obtain TSTA (1.04 g, yield=82%) as yellow solid.

Aufarbeitung

  1. waitfollowed by 1 h at room temperature
  2. extractionThe solution mixture was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-93d90e8adf0a408eadb3605458564425
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08974920B2

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