Morpholine → 4-[(5-Bromothiophen-2-yl)methyl]morpholine

HRID 2421340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421340
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:7][C:8]1(C=O)[CH2:12][CH:11]=C[S:9]1.C(O[BH-](O[C:25](=O)[CH3:26])OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:7][C:8]1[S:9][C:25]([CH2:26][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866100842-Bromothiophene carboxaldehyde

Produkt 1

HCID 219142724-[(5-Bromothiophen-2-yl)methyl]morpholineAusbeute 148,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Morpholine (0.96 g) was added portionwise to a solution of 2-bromothiophene carboxaldehyde (1.195 g) in tetrahydrofuran (50 ml). After stirring at room temperature for 5 minutes, sodium triacetoxyborohydride (3.18 g) was added and the mixture stirred at room temperature for a further 3 h. The mixture was added to saturated aqueous sodium bicarbonate (100 ml) and extracted twice with ethyl acetate. The combined extracts were evapourated to dryness. The product was purified by column chromatography elutinig with ethyl acetate in hexane mixtures to give a yellow oil (2.414 g).

Aufarbeitung

  1. stirringthe mixture stirred at room temperature for a further 3 h
  2. extractionextracted twice with ethyl acetate
  3. customThe product was purified by column chromatography elutinig with ethyl acetate in hexane mixtures

Quellen und Nachweise

ORD-Eintrag
ord-91b4b598c0d143028677f86a1adab658
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956084B2

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