1-Tert-butyl 3-ethyl 2-(6-nitropyridin-3-yl)malonate → Ethyl 2-(6-nitropyridin-3-yl)acetate

HRID 2173311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173311
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([CH:10](C(OCC)=O)[C:11]([O:13][C:14](C)(C)[CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N+:1]([C:4]1[N:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

3

Edukt 1

HCID 673939371-Tert-butyl 3-ethyl 2-(6-nitropyridin-3-yl)malonate

Produkt 1

HCID 21300451Ethyl 2-(6-nitropyridin-3-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl ethyl (6-nitropyridin-3-yl)propanedioate (1.4 g, 4.5 mmol) in a mixed solution of TFA/DCM (10 mL/10 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 ethyl (6-nitropyridin-3-yl)acetate. 1H-NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.27 (d, J=8.4 Hz, 1H), 8.03 (dd, J=2.4 Hz, 8.4 Hz, 1H), 4.22 (q, J=7.2 Hz, 2H), 3.81 (s, 2H), 1.30 (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-ef1b3569fe3340988f3a2321f86bf2f1
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056859B2

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