1-Ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrole-2-carboxylic acid methyl amide → 1-[1-Ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrol-2-yl]-propan-1-one

HRID 646248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646248
CN[C:3]([C:5]1[N:6]([CH2:20][CH3:21])[CH:7]=[C:8]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH:9]=1)=[O:4].[CH3:22][CH2:23][Mg+].[Br-]>C1COCC1>[CH2:20]([N:6]1[CH:7]=[C:8]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH:9]=[C:5]1[C:3](=[O:4])[CH2:22][CH3:23])[CH3:21]

Komponenten

4

Edukt 2

HCID 686995231-Ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrole-2-carboxylic acid methyl amideHCID 178461630HCID 178461630, Verbindung

Produkt 1

HCID 686988131-[1-Ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrol-2-yl]-propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere to a cold (0° C.) solution of 1-ethyl-4-(3-methoxy-phenylethynyl)-1H-pyrrole-2-carboxylic acid methyl amide (2.48 g, 7.93 mmol) in THF (40 ml) was added EtMgBr solution (1 molar in THF, 16 mL) over 10 minutes. The mixture was allowed to warm to room temperature and stirred for 18 hours, then poured into ice/1 N HCl solution and extracted with ether. The combined ether extracts were washed with brine, dried over MgSO4 and evaporated to dryness. The resultant residue was purified by flash chromatography (hexane/ethyl acetate 9.5/0.5) to give the title compound as an off white solid (1.8 g, 80% yield), mp 64° C., 1H NMR (400 MHZ, CDCl3) δ 1.16 (t, 3H), 1.35 (t, 3H), 2.8 (q, 2H), 3.79 (s, 3H), 4.35 (q 2H), 6.85 (m, 1H), 6.99-7.03 (m, 2H), 7.05 (m, 2H), 7.08 (m, 1H), MS m/e (M+H)+ 282.1.

Aufarbeitung

  1. extractionextracted with ether
  2. washThe combined ether extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe resultant residue was purified by flash chromatography (hexane/ethyl acetate 9.5/0.5)

Quellen und Nachweise

ORD-Eintrag
ord-09e7833062474f83a242614dadeee947
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705030B2

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