Sodium Bicarbonate → 6-Benzyloxy-2-(4-benzyloxyphenyl)-1-ethylindolizine

HRID 1422076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1422076
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH3:17])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:25][C:26]1[CH:35]=[CH:34][C:29]([C:30](=O)[CH2:31]Br)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([CH:31]=[C:30]([C:29]3[CH:34]=[CH:35][C:26]([O:25][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:27][CH:28]=3)[C:15]=2[CH2:16][CH3:17])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-oneHCID 187069675-Benzyloxy-2-n-propylpyridine

Produkt 1

HCID 187070166-Benzyloxy-2-(4-benzyloxyphenyl)-1-ethylindolizineAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

5-Benzyloxy-2-n-propylpyridine (50.15 g, 221 mmol) and 4-benzyloxyphenacylbromide (67.34 g, 221 mmol) was dissolved in 400 ml of dry acetone under a nitrogen atmosphere. The mixture was heated to reflux for 5 days. The reaction was cooled to room temperature and the solvent was removed. The remaining quaternary salt was suspended in 250 ml of water and 250 ml of diethyl ether and filtered off. The dried salt was suspended in 600 ml of water and sodium hydrogen carbonate (74 g, 884 mmol) was added. The mixture was refluxed for 3 days. The resulting precipitate was filtered off, washed with water and dried to afford 75.38 g (78%) of 6-benzyloxy-2-(4-benzyloxyphenyl)-1-ethylindolizine as brown crystals. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.10 (t, 3H); 2.79 (q, 2H); 5.02 (s, 2H); 5.12 (s, 2H); 6.52 (dd, 1H); 7.08 (d, 2H); 7.29-7.51 (m, 14H); 7.96 (s, 1H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 days
  3. customthe solvent was removed
  4. filtration250 ml of diethyl ether and filtered off
  5. temperatureThe mixture was refluxed for 3 days
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-233019f78ace43bfa337e53ac350218b
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06080754

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