Diisopropylethylamine → Ethyl 1-benzyloxymethyl-2-formyl-1H-pyrrol-3-carboxylate

HRID 2097521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2097521
[CH2:1]([O:8][CH2:9][N:10]1[C:14](Br)=[CH:13][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:11]1[CH:21]=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[H][H]>[Pd].C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:11]1[CH:21]=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 86627040Ethyl 1-benzyloxymethyl-5-bromo-2-formyl-1H-pyrrol-3-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86627045Ethyl 1-benzyloxymethyl-2-formyl-1H-pyrrol-3-carboxylateAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To 43 ml of toluene solution containing 3.66 g (10.0 mmol) of ethyl 1-benzyloxymethyl-5-bromo-2-formyl-1H-pyrrol-3-carboxylate obtained in Reference example 17-(c) were added 2.1 ml of N,N-diisopropylethylamine and 0.4 g of 5% palladium-active carbon, and the mixture was stirred under 1 atm hydrogen atmosphere at room temperature for 6 hours. After completion of the reaction, insoluble material was removed by filtration from the reaction mixture, ethyl acetate was added to the filtrate, and the filtrate was washed successively with water and a saturated aqueous solution of sodium chloride. The organic layer after separation was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 2.96 g the title compound as a pale yellowish solid substantially quantitatively.

Aufarbeitung

  1. customAfter completion of the reaction, insoluble material
  2. customwas removed by filtration from the reaction mixture, ethyl acetate
  3. additionwas added to the filtrate
  4. washthe filtrate was washed successively with water
  5. customThe organic layer after separation
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6f3cd7db2f1243ceb8c70e9d16887767
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450319B2

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