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Diethyl Ether → ethyl 5-{(2RS,3RS)-3-amino-2-(4-nitrophenyl)butyl}-2-furancarboxylate

HRID 581040
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 581040
[N:1]([CH:4]([CH3:26])[CH:5]([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)[CH2:6][C:7]1[O:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C>O1CCCC1.O>[NH2:1][CH:4]([CH3:26])[CH:5]([C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)[CH2:6][C:7]1[O:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 54125754ethyl 5-{(2RS,3RS)-3-azido-2-(4-nitrophenyl)butyl}-2-furancarboxylate

Produkt 1

HCID 53734556ethyl 5-{(2RS,3RS)-3-amino-2-(4-nitrophenyl)butyl}-2-furancarboxylateAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962Water
Lösungsmittel
2×
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3.24 g of ethyl 5-{(2RS,3RS)-3-azido-2-(4-nitrophenyl)butyl}-2-furancarboxylate was dissolved in a mixed solution of 50 ml of tetrahydrofuran and 5 ml of water, and 2.37 g of triphenylphosphine was added thereto, followed by heating and refluxing for 6 hours. The reaction solution was left to cool to room temperature, and then ethyl ether and water were added thereto for extraction. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1+20/1) to obtain 2.89 g of the above-identified compound.

Aufarbeitung

  1. additionwas added
  2. temperatureby heating
  3. temperaturerefluxing for 6 hours
  4. waitThe reaction solution was left
  5. extractionfor extraction
  6. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1+20/1)

Quellen und Nachweise

ORD-Eintrag
ord-9f33cc1b1a0d4ef5b4402c31df59d396
Quelldatensatz
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05919786

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