Pyrrole-2-carboxaldehyde → 1-[2-Nitro-5-(ethoxycarbonyl)benzyl]-pyrrole-2-carboxaldehyde

HRID 3602

Reaktionsgleichung

Reaktionsgleichung von HRID 3602
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]=[O:9].[N+:10]([C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][C:14]=1[CH2:24]Br)([O-:12])=[O:11]>O1CCCC1>[N+:10]([C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][C:14]=1[CH2:24][N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH:8]=[O:9])([O-:12])=[O:11]

Komponenten

5

Edukt 3

HCID 13854Pyrrole-2-carboxaldehydeHCID 24758Sodium hydrideHCID 130774453-Bromomethyl-4-nitro-benzoic acid ethyl ester

Produkt 1

HCID 218371151-[2-Nitro-5-(ethoxycarbonyl)benzyl]-pyrrole-2-carboxaldehydeAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a stirred slurry of 2.2 g of sodium hydride (60% in oil, washed with hexane) in tetrahydrofuran is added at 0° C. a solution of 4.5 g of pyrrole-2-carboxaldehyde in 25 ml of tetrahydrofuran. After the addition is complete, a solution of 15 g of ethyl 4-nitro-3-bromomethylbenzoate in 30 ml of dry tetrahydrofuran is slowly added under nitrogen. The reaction mixture is stirred at 20° C. for 8 hours and carefully quenched with water. The reaction mixture is extracted with chloroform which is washed with water, dried with Na2SO4 and concentrated in vacuo to give 12 g of the desired product as a solid; mass spectrum (M+ H)349.

Aufarbeitung

  1. additionAfter the addition
  2. customcarefully quenched with water
  3. extractionThe reaction mixture is extracted with chloroform which
  4. washis washed with water
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-169b2f504f264086a66d2edfe51fb873
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733905

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