Pyrrolidine → 2-Pyrrolidin-1-yl-5-thiophen-2-yl-benzaldehyde

HRID 10683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 10683
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:3]=1[CH:4]=[O:5].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C(OCC)(=O)C>[N:15]1([C:2]2[CH:9]=[CH:8][C:7]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

4

Edukt 2

HCID 31268PyrrolidineHCID 167686562-Fluoro-5-(thiophen-2-yl)benzaldehyde

Produkt 1

HCID 219810662-Pyrrolidin-1-yl-5-thiophen-2-yl-benzaldehydeAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ex-63A: A solution of 2-fluoro-5-thiophen-2-yl-benzaldehyde (1.42 g, 6.89 mmol) in pyrrolidine was refluxed (10 mL). After 4.5 days the reaction mixture was cooled and diluted with ethyl acetate. The solution of ethyl acetate was washed with hydrochloric acid (0.5M) sodium carbonate (2M) and saturated solution of sodium bicarbonate, dried over sodium sulfate, and concentrated. The crude product was purified by flash chromatography. Elution with ethyl acetate (20%, v/v, in hexane) afforded 2-pyrrolidin-1-yl-5-thiophen-2-yl-benzaldehyde (0.5 g, 32%). 1H NMR (CDCl3) δ 10.14 (s, 1H), 7.94 (d, J=2 Hz, 1H), 7.62 (dd, J=2.7, 9 Hz, 1H), 7.22–7.20 (m, 2H), 7.07–7.04 (m, 1H), 6.86 (d, J=9 Hz, 1H), 3.41 (m, 4H), 2.01 (m, 4H).

Aufarbeitung

  1. temperatureAfter 4.5 days the reaction mixture was cooled
  2. washThe solution of ethyl acetate was washed with hydrochloric acid (0.5M) sodium carbonate (2M) and saturated solution of sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography
  6. washElution with ethyl acetate (20%, v/v, in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-db9d400ae05d48d8a73cef95d7c4ce31
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

Notizen zur Reaktion

Wird geladen…