تفاعل #43340

ord-bbb5dbd2e2ab41958523662e95cd9384

معادلة التفاعل

C1=COCCC1
3,4-Dihydro-2H-pyran
Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1
pyridinium p-toluenesulfonate
ClC(Cl)Cl
chloroform
COc1cc(Br)ccc1O
4-bromo-2-methoxyphenol
COc1cc(Br)ccc1OC1CCCCO1
title compound
المردود 86.0%
COc1cc(Br)ccc1OC1CCCCO1
2-(4-bromo-2-methoxyphenoxy)tetrahydro-2H-pyran
المردود 86.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصfollowed by extraction with chloroform
  2. 2
    غسيلThe organic layer was washed with water
  3. 3
    تجفيفdried over anhydrous magnesium sulfate
  4. 4
    تركيزConcentrating the solvent under reduced pressure
  5. 5
    أخرىthe residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19)

الإجراء التجريبي

3,4-Dihydro-2H-pyran (2.0 mL) and pyridinium p-toluenesulfonate (370 mg) were added to chloroform solution (30 mL) of 4-bromo-2-methoxyphenol (3.0 g) and stirred at room temperature for 12 hours. Saturated brine was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with water and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19) to provide the title compound (3.64 g, 86%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07732456B2uspto-grants-2010_06