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1,1,3,3-Tetramethylguanidine → (z)-2-Ethoxy-3-(1h-indol-4-yl)-acrylic acid ethyl ester

HRID 11380
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 11380
[Cl-].[CH2:2]([O:4][CH:5]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:3].CN(C)C(=N)N(C)C.[CH:38]([C:40]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:41]=1[CH:42]=[CH:43][NH:44]2)=O>ClCCl>[CH2:9]([O:8][C:6](=[O:7])/[C:5](/[O:4][CH2:2][CH3:3])=[CH:38]/[C:40]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:41]=1[CH:42]=[CH:43][NH:44]2)[CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 664601,1,3,3-Tetramethylguanidine2×HCID 333703Indole-4-carboxaldehydeHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)

Produkt 1

HCID 69280560(z)-2-Ethoxy-3-(1h-indol-4-yl)-acrylic acid ethyl esterAusbeute 107,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of 35.01 g (81.6 mmol) of (1,2-diethoxy-2-oxoethyl)triphenyl phosphonium chloride in 200 ml of dichloromethane was added at 0° C. 11.01 ml (87.1 mmol) of tetramethyl guanidine and the mixture was warmed to 22° C. The mixture was treated with 7.9 g (54.4 mmol) of 4-formyl-indole and stirring was continued at 40° C. for 16 h. The mixture was treated again with 10.0 g (23.3 mmol) of the Wittig salt and 8.0 ml (24.0 mmol) of tetramethyl guanidine and stirring was continued at 40° C. for 24 h after which time the conversion was complete. The reaction mixture was poured into crashed ice and then extracted twice with MeCl2. The organic layer was washed with water, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica (n-heptane/AcOEt, 95:5 to 4:1) to give 15.12 g of the title compound as a light yellow solid.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued at 40° C. for 24 h
  3. additionThe reaction mixture was poured
  4. extractionextracted twice with MeCl2
  5. washThe organic layer was washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed on silica (n-heptane/AcOEt, 95:5 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-5c81a3b3502a410b88b65a8da4ebe4d9
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07098228B2

Notizen zur Reaktion

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