Sodium hydride → (E)-3-(2'-tert-butoxycarbonyl-ethenyl)-4,6-dichloro-1H-indole-2-carboxylic acid isopropyl ester

HRID 581060

Reaktionsgleichung

Reaktionsgleichung von HRID 581060
[H-].[Na+].[Br-].[C:4]([O:8][C:9]([CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:10])([CH3:7])([CH3:6])[CH3:5].[H][H].[CH2:33]([O:35][C:36]([C:38]1[NH:39][C:40]2[C:45]([C:46]=1[CH:47]=O)=[C:44]([Cl:49])[CH:43]=[C:42]([Cl:50])[CH:41]=2)=[O:37])[CH3:34].[C:51](OC(C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)(C)(C)C>C(O)(C)C.O>[CH:33]([O:35][C:36]([C:38]1[NH:39][C:40]2[C:45]([C:46]=1/[CH:47]=[CH:11]/[C:9]([O:8][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:10])=[C:44]([Cl:49])[CH:43]=[C:42]([Cl:50])[CH:41]=2)=[O:37])([CH3:51])[CH3:34]

Komponenten

8

Edukt 5

HCID 24758Sodium hydrideHCID 256127tert-Butyl (triphenylphosphoranylidene) acetate2×HCID 2733853(tert-Butoxycarbonylmethyl)triphenylphosphonium BromideHCID 2794948ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67558194(E)-3-(2'-tert-butoxycarbonyl-ethenyl)-4,6-dichloro-1H-indole-2-carboxylic acid isopropyl esterAusbeute 207,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Sodium hydride (1 g; 95%) was added in two 0.5 g portions to a solution of (tert-butoxycarbonylmethyl)-triphenylphosphonium bromide (8.4 g) in isopropanol (100 ml). After the evolution of hydrogen ceased ethyl-3-formyl-4,6-dichloro-indole-2-carboxylate (5 g) was added and the reaction mixture was refluxed for 2 h. (tert-Butoxycarbonylmethylene)-triphenylphosphorane (1 g) was added and the reflux was continued for 8 h. An other amount of (tert-butoxycarbonylmethylene)-triphenylphosphorane (3.5 g) was added and the reaction mixture was refluxed for additional 3 h. After cooling to r.t. the solution was poured into water and extracted with ethyl acetate. The organic extracts were dried and evaporated under reduced pressure. The residue was purified by flash chromatography using cyclohexane/ethyl acetate 3:1 as eluant to give the title compound (2.2 g) as a white solid.

Aufarbeitung

  1. additionwas added
  2. additionwas added
  3. temperaturethe reaction mixture was refluxed for additional 3 h
  4. extractionextracted with ethyl acetate
  5. customThe organic extracts were dried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-69d1d42198544a6ca32a38130fded35b
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919811

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