Trifluoroacetic acid methylene chloride → Ethyl 2-(5-nitropyridin-2-YL)acetate

HRID 1502107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502107
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10](C(OCC)=O)[C:11]([O:13][C:14](C)(C)[CH3:15])=[O:12])=[N:8][CH:9]=1)([O-:3])=[O:2].C(O)(C(F)(F)F)=O.C(Cl)Cl>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

3

Edukt 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 54383765tert-Butyl ethyl (5-nitropyridin-2-yl)malonate

Produkt 1

HCID 18670679Ethyl 2-(5-nitropyridin-2-YL)acetate

Versuchsvorschrift

A mixture of tert-butyl ethyl (5-nitropyridin-2-yl)propanedioate (4.10 g, 13.2 mmol) in a mixed solution of TFA/DCM (4 mL/20 mL) was stirred for 5 hours at room temperature. The mixture was concentrated under reduce pressure. The residue was dissolved with DCM, washed with sat. NaHCO3, dried over anhydrous Na2SO4 and concentrated to give title compound. 1H-NMR (400 MHz, CDCl3) δ 9.41 (s, 1H), 8.58 (d, J=8.4 Hz, 1H), 7.64 (d, J=8.4 Hz, 1H), 4.16 (q, J=7.2 Hz, 2H), 4.02 (s, 2H), 1.22 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved with DCM
  3. washwashed with sat. NaHCO3
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-210190040cf24f68a7e67045266c73cc
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206199B2

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