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N,N-Dimethylglycine → trans-Stilbene

HRID 429610
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 429610
CN(C)[CH2:3][C:4](O)=O.[C:8]([O-])(=O)[CH3:9].[Na+].CN1[C:18](=O)[CH2:17][CH2:16][CH2:15]1.[CH2:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>[P+](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl-].C(OCC)C>[C:22]1(/[CH:21]=[CH:20]/[C:4]2[CH:3]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:22]1(/[CH:21]=[CH:20]\[C:8]2[CH:9]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:22]1([C:21]([C:4]2[CH:3]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH2:20])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 673N,N-DimethylglycineHCID 7501StyreneHCID 13387N-methyl-2-pyrrolidone2×HCID 517045Sodium Acetate

Produkt 3

HCID 107401,1-DiphenylethyleneHCID 638088trans-StilbeneAusbeute 97,4 %
HCID 5356785
cis-Stilbene
Ausbeute 0,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 164911Tetraphenylphosphonium ChlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a reaction vessel standing on a scale which is sealed with a septum cap, 5.3 mg (0.02 mmol) of (CH3CN)2PdCl2, 45 mg (0.12 mmol) of Ph4PCl and 12.4 mg (0.12 mmol) of dimethylglycine are added, followed by two cycles of evacuation and flushing with argon. Under argon, 657.7 mg (8 mmol) of anhydrous sodium acetate and 1 ml of NMP are added. 452 mg (4.01 mmol) of Cl-benzene and 636 mg (6.11 mmol) of styrene is mixed with 1 ml of NMP and added dropwise in 6 portions within 6 hours, the first portion being added at room temperature and the others at 140° C. Stirring is performed at 140° C. for a total of 24 h. According to the processing described in Example 1 using 10 ml of diethyl ether, a 64.2% yield of Heck products (97.4% trans-stilbene, 0.6% cis-stilbene, and 2.0%- 1,1-diphenylethene) is obtained with 76.6% conversion of Cl-benzene.

Aufarbeitung

  1. customTo a reaction vessel standing on a scale which
  2. customis sealed with a septum
  3. customcap
  4. customflushing with argon
  5. additionadded dropwise in 6 portions within 6 hours
  6. additionthe first portion being added at room temperature
  7. customat 140° C
  8. customis performed at 140° C. for a total of 24 h

Quellen und Nachweise

ORD-Eintrag
ord-d92d3569a6cc478798316003861e97d6
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06316675B1

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