Dimedone → HCID 44136863, Verbindung

HRID 1020278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020278
[CH3:1][C:2]1([CH3:10])[CH2:9][C:7](=[O:8])[CH2:6][C:4](=O)[CH2:3]1.[C:11]1([C:17]2[S:21][C:20]([CH:22]=O)=[CH:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:24]([CH2:27][C:28](=O)[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:25]C.C([O-])(=O)C.[NH4+:40]>C(O)C.C(OCC)(=O)C>[CH3:10][C:2]1([CH3:1])[CH2:3][C:4]2[NH:40][C:28]([CH2:27][CH2:24][CH3:25])=[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:22]([C:20]3[S:21][C:17]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[CH:18][CH:19]=3)[C:6]=2[C:7](=[O:8])[CH2:9]1

Komponenten

7

Edukt 4

HCID 31358DimedoneHCID 1770535-Phenylthiophene-2-carbaldehydeHCID 517165Ammonium AcetateHCID 559036Ethyl 3-oxoheptanoate

Produkt 1

HCID 44136863HCID 44136863, VerbindungAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of dimedone (0.70 g, 5.0 mmole) in hot ethanol (15 ml) was added 5-phenyl-2-thiophenecarboxaldehyde (0.940 g, 5.0 mmole), ethyl propylacetoacetate (0.80 ml, 5.0 mmole) and lastly ammonium acetate (0.770 g, 10.0 mmole). The mixture was held at reflux for 48 h. No precipitate was observed. The ethanol was removed in vacuo to provide a crude viscous material which was subjected to a 100 g SiO2 flash column using 40% ethyl acetate:hexanes as eluent. The desired product (1.54 g, 68%) was obtained as a yellow amorphous solid. Rf=0.37 in 1:1 ethyl acetate hexanes. 1H NMR (400 MHz; CDCl3) d 7.5 (bd, 2H, J=7.0 Hz); 7.32-7.25 (m, 2H); 7.19 (at, 1H, J=7.4 Hz); 7.04 (d, 1H, J=7.4 Hz); 6.8 (d, 1H, J=3.5 Hz); 6.38 (bs, 1H); 5.41 (s, 1H); 4.22-3.90 (m, 2H); 2.90-2.80 (m, 1H); 2.72-2.63 (m, 1H); 2.35 (d, 1H, J=16.8 Hz); 2.25 (d, 1H, J=16.8 Hz); 2.3-2.2 (On, 2H); 1.74-1.62 (m, 2H); 1.25 (at, 3H, J=7.0 Hz); 1.07 (s, 3H); 1.02 (s, 3H); 1.01 (at, 3H, J=7.0 Hz); 1.05-0.95 (m, 2H). LC MS shows MH+ at 450; 2M+H at 899 and 2M+Na at 921.

Aufarbeitung

  1. temperatureat reflux for 48 h
  2. customThe ethanol was removed in vacuo
  3. customto provide a crude viscous material which

Quellen und Nachweise

ORD-Eintrag
ord-413fb2d6373d4677baa89c69490d54cc
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716319B2

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