Aluminium lithium hydride → (1-benzyl-3-nitro-1H-pyrazol-4-yl)methanol

HRID 1426270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426270
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13](OCC)=[O:14])[C:10]([N+:18]([O-:20])=[O:19])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[C:10]([N+:18]([O-:20])=[O:19])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 67963011ethyl 1-benzyl-3-nitro-1H-pyrazole-4-carboxylate

Produkt 1

HCID 67963013(1-benzyl-3-nitro-1H-pyrazol-4-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

A solution of C2 (1.35 g, 4.90 mmol) in tetrahydrofuran (40 mL) was cooled to −40° C. and treated with lithium aluminum hydride (99%, 1 M, 10.3 mL, 10.3 mmol). The reaction was allowed to stir for 20 minutes at −40° C., then was quenched with saturated aqueous ammonium chloride solution. After addition of EtOAc and water, the layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to provide C3 as a solid. Yield: 1.29 g, 5.53 mmol, quantitative. 1H NMR (500 MHz, CDCl3) δ 2.63 (br t, J=6 Hz, 1H), 4.79 (br d, J=5.4 Hz, 2H), 5.33 (s, 2H), 7.29-7.32 (m, 2H), 7.36-7.41 (m, 3H), 7.42 (s, 1H).

Aufarbeitung

  1. customwas quenched with saturated aqueous ammonium chloride solution
  2. additionAfter addition of EtOAc and water
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-880067be088c4acfb11687cc909b4a8e
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933095B2

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