Sodium hydride → ethyl 4-(4-chlorophenyl)-1H-pyrrole-3-carboxylate

HRID 1651697

Reaktionsgleichung

Reaktionsgleichung von HRID 1651697
[H-].[Na+].[Cl:3][C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1.C1(C)C=CC(S([CH2:26][N+:27]#[C-:28])(=O)=O)=CC=1>CCOCC.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:26][NH:27][CH:28]=2)=[CH:15][CH:16]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 2014712-Propenoic acid, 3-(4-chlorophenyl)-, ethyl ester

Produkt 1

HCID 470434ethyl 4-(4-chlorophenyl)-1H-pyrrole-3-carboxylateAusbeute 25,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a mixture of 5.63 g of a 60% sodium hydride/oil suspension in 200 mL of dry ether under nitrogen is added from an additional funnel a mixture of 23.5 g (122 mmol) of ethyl p-chlorocinnamate and 19.4 g (122 mmol) of (p-tolylsulfonyl)methyl isocyanide in solution in 180 mL of ether and 80 mL of dimethylsulfonide. The addition time is about 20 minutes and results in gentle refluxing of the mixture. After another 10 minutes stirring, the mixture is diluted with 100 mL of water. The mixture is extracted four times with ether which is then dried over magnessium sulfate followed by concentrated in vacuo. The resulting solid is recrystallized from ethylene dichlorite to give 7.8 g of crystals, m.p. 137°-138° C.

Aufarbeitung

  1. additionis added from an additional funnel
  2. customresults
  3. temperaturein gentle refluxing of the mixture
  4. extractionThe mixture is extracted four times with ether which
  5. dry with materialis then dried over magnessium sulfate
  6. concentrationby concentrated in vacuo
  7. customThe resulting solid is recrystallized from ethylene dichlorite

Quellen und Nachweise

ORD-Eintrag
ord-7afcc8742b304d3893d682373928c3ba
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04929634

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