Nitrogen → HCID 66928816, Verbindung

HRID 2064915

Reaktionsgleichung

Reaktionsgleichung von HRID 2064915
N#N.C[O:4][C:5]([C:7]1[O:8][C:9]([CH2:12][N:13]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[N:14]2)=[CH:10][CH:11]=1)=O.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.C1(C)C=CC=CC=1>[N+:18]([C:16]1[CH:15]=[N:14][N:13]([CH2:12][C:9]2[O:8][C:7]([CH2:5][OH:4])=[CH:11][CH:10]=2)[CH:17]=1)([O-:20])=[O:19]

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 3157344Methyl 5-[(4-nitro-1h-pyrazol-1-yl)methyl]-2-furoate

Produkt 1

HCID 66928816HCID 66928816, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(4-nitro-pyrazol-1-ylmethyl)-furan-2-carboxylic acid methyl ester (10.0 g, 39.81 mmol) in THF (300.0 mL) was treated dropwise, at −78° C. with DiBAL (160.0 mL of a 1M solution in toluene, 160.0 mmol). The reaction mixture was stirred at −78° C. for 1.5 h and at rt for 1 h. Sat. aq. Rochelle's salt (600 mL) was added and the reaction mixture was stirred at rt for 1 h. The aq. layer was extracted with EA (2×350 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (40:60 hept-EA) gave the title compound. TLC: rf (40:60 hept-EA)=0.28. LC-MS-conditions 02: tR=0.74 min. 1H NMR (400 MHz, CDCl3) δ 2.10 (s, 1H), 4.62 (s, 2H), 5.31 (s, 2H), 6.33 (d, J=3.0 Hz, 1H), 6.47 (d, J=3.0 Hz, 1H), 8.08 (s, 1H), 8.15 (s, 1H).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at rt for 1 h
  2. extractionThe aq. layer was extracted with EA (2×350 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (40:60 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-24315651279e4259a0eb3d21097db83e
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288419B2

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