Sodium Iodide → 2-[4-[[4-(2-Iodoethoxy)phenyl]methyl]phenyl]oxazole

HRID 1046318

Reaktionsgleichung

Reaktionsgleichung von HRID 1046318
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:19][CH:20]=[CH:21][N:22]=3)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.[I-:23].[Na+]>CC(=O)CC>[I:23][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:19][CH:20]=[CH:21][N:22]=3)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 684847252-[4-[[4-(2-Chloroethoxy)phenyl]methyl]phenyl]oxazole

Produkt 1

HCID 684895932-[4-[[4-(2-Iodoethoxy)phenyl]methyl]phenyl]oxazoleAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A solution of 2-[4-[[4-(2-chloroethoxy)phenyl]methyl]phenyl]oxazole (1.7 g, 4.4 mmol) in 2-butanone (18 mL) was stirred as sodium iodide (7 g, 44 mmol) was added. The reaction was heated at reflux for 2 days. The reaction was concentrated. The residue was dissolved in ethyl acetate and washed with water. The combined organic layers were dried and concentrated. The residue was recrystallized from methanol to give 1.4 g of 2-[4-[[4-(2-iodoethoxy)phenyl]methyl]phenyl]oxazole, 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 2H), 7.68 (s, 1H), 7.27 (d, 2H), 7.21 (s, 1H), 7.13 (d, 2H), 6.82 (d, 2H), 4.22 (t, 2H), 3.96 (s, 2H), 3.39 (t, 2H).

Aufarbeitung

  1. additionwas added
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 2 days
  4. concentrationThe reaction was concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water
  7. customThe combined organic layers were dried
  8. concentrationconcentrated
  9. customThe residue was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-afb24c0f717449c3a92dbfee88907820
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569303B2

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