تفاعل #44787

ord-c4f73b96e4cc4bb3806897b156366a96

معادلة التفاعل

ClCCOc1ccc(Cc2ccc(-c3ncco3)cc2)cc1
2-[4-[[4-(2-chloroethoxy)phenyl]methyl]phenyl]oxazole
[I-].[Na+]
sodium iodide
ICCOc1ccc(Cc2ccc(-c3ncco3)cc2)cc1
2-[4-[[4-(2-iodoethoxy)phenyl]methyl]phenyl]oxazole
المردود 78.5%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONwas added
  2. 2
    درجة الحرارةThe reaction was heated
  3. 3
    درجة الحرارةat reflux for 2 days
  4. 4
    تركيزThe reaction was concentrated
  5. 5
    workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
  6. 6
    غسيلwashed with water
  7. 7
    أخرىThe combined organic layers were dried
  8. 8
    تركيزconcentrated
  9. 9
    أخرىThe residue was recrystallized from methanol

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07737145B2uspto-grants-2010_06