Acetic Acid → Diethyl 2-((dimethylamino)methylene)-3-oxosuccinate

HRID 920720

Reaktionsgleichung

Reaktionsgleichung von HRID 920720
[Na].[C:2]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:3][C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:5].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19].C(O)(=O)C>C(O)C>[CH3:17][N:18]([CH:20]=[C:3]([C:4](=[O:5])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:2]([O:12][CH2:13][CH3:14])=[O:11])[CH3:19]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 78373Dimethylformamide dimethyl acetalHCID 57351814Diethyl 2-oxosuccinate,sodium salt

Produkt 1

HCID 72733183Diethyl 2-((dimethylamino)methylene)-3-oxosuccinateAusbeute 37,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of diethyl oxalacetate sodium salt (100 g, 476 mmol) in ethanol (250.00 mL) was added 1,1-dimethoxy-N,N-dimethylmethanamine (113 g, 952 mmol) and the reaction was stirred at room temperature for 30 min. Acetic acid (54.5 mL, 952 mmol) was added slowly over a period of 3 h and stirred at room temperature for 24 h. The volatile components were evaporated under reduced pressure and the oily residue was purified by silica gel chromatography (750 g REDISEP® column, eluting with 30% EtOAc in hexane). Fractions containing the product were combined and evaporated to afford Intermediate 104A (43 g, 30.8%). MS(ES): m/z=244 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 7.84 (s, 1H), 4.31 (q, J=7.2 Hz, 2H), 4.18 (q, J=5.4 Hz, 2H), 3.35 (s, 3H), 3.04 (s, 3H), 1.36 (t, J=7.2 Hz, 3H), 1.26 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. stirringstirred at room temperature for 24 h
  2. customThe volatile components were evaporated under reduced pressure
  3. customthe oily residue was purified by silica gel chromatography (750 g REDISEP® column, eluting with 30% EtOAc in hexane)
  4. additionFractions containing the product
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-dc60b8c4541f4c00bc1f84aaf85d22bf
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273058B2

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