Dimethylformamide dimethyl acetal → HCID 10975874, Verbindung

HRID 1478238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478238
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][N+:6]#[C-:7])[CH3:2].CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>C(O)C>[CH2:1]([O:3][C:4](=[O:8])/[C:5](/[N+:6]#[C-:7])=[CH:11]/[N:12]([CH3:14])[CH3:13])[CH3:2]

Komponenten

4

Edukt 2

HCID 78373Dimethylformamide dimethyl acetalHCID 533707Ethyl isocyanoacetate

Produkt 1

HCID 10975874HCID 10975874, VerbindungAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl-2-isocyanoacetate (10.3 g, 91 mmol) in ethanol (100 ml) was cooled down to 0° C. 1,1-dimethoxy-N,N-dimethyl methanamine (26.6 ml, 200 mmol) was added and the reaction mixture was then allowed to reach RT and stirred for 24 h. The mixture was concentrated and the crude material was purified by flash chromatography (heptane/EtOAc, 100:0 to 40:60) to afford 11 g (64.7 mmol, 71.1% yield) of the title compound. LCMS: (M+H)=169; tR=0.74 min (LC-MS 2); 1H-NMR (CDCl3, 400 MHz) δ (ppm) 7.15 (s, 1H), 4.18 (q, 2H), 3.20 (bs, 6H), 1.26 (t, 3H).

Aufarbeitung

  1. customto reach RT
  2. concentrationThe mixture was concentrated
  3. customthe crude material was purified by flash chromatography (heptane/EtOAc, 100:0 to 40:60)

Quellen und Nachweise

ORD-Eintrag
ord-07c576ca91d9475181cce6374cdb3277
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403827B2

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