Diisobutylaluminumhydride → (5-Nitropyridin-2-yl)methanol

HRID 43151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43151
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1)=O)C>C(Cl)Cl>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:14][OH:13])=[N:17][CH:18]=1)([O-:24])=[O:23]

Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 45116302Ethyl 5-nitropicolinate

Produkt 1

HCID 20583228(5-Nitropyridin-2-yl)methanolAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Diisobutylaluminium hydride (1 M in DCM, 41.6 mL, 41.6 mmol, 1.3 equiv) was added dropwise to a cold (−78° C.) solution of 5-nitro-pyridine-2-carboxylic acid ethyl ester (Step 39.4) (6.4 g, 32 mmol) in DCM (120 mL), under an argon atmosphere. The reaction mixture was allowed to warm to rt, quenched by addition of an aqueous solution of potassium sodium tartrate, diluted with DCM and H2O, and filtered through a pad of celite. The filtrate was extracted several times with DCM. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 9:1→1:1) to provide 1.44 g of the title compound: ESI-MS: 153.1 [M−H]−.

Aufarbeitung

  1. customquenched by addition of an aqueous solution of potassium sodium tartrate
  2. additiondiluted with DCM and H2O
  3. filtrationfiltered through a pad of celite
  4. extractionThe filtrate was extracted several times with DCM
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 9:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-062a8fa1bf754846b758e3effd466d29
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536175B2

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