تفاعل #331838

ord-44af04039a3743b0802e6c9f74901296

المذيبات

ظروف التفاعل

درجة الحرارة
100°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةthe mixture heated at 100° C. under microwave irradiation for 60 min
  2. 2
    درجة الحرارةthe mixture heated at 100° C. under microwave irradiation for 60 min
  3. 3
    درجة الحرارةthe mixture heated at 100° C. under microwave irradiation for 60 min
  4. 4
    أخرىThe solvent was removed in vacuo
  5. 5
    أخرىthe residue was partitioned between DCM (15 ml) and water (15 ml)
  6. 6
    أخرىseparated
  7. 7
    استخلاصThe aqueous layer was extracted with dichloromethane (2×5 ml)
  8. 8
    تركيزthe combined organic layers were concentrated in vacuo
  9. 9
    أخرىPurification by chromatography on silica gel (20 g silica cartridge)
  10. 10
    غسيلeluting with a gradient of 0-50% DCM in cyclohexane over 20 minutes

الإجراء التجريبي

A microwave vial was charged with ethyl 1-(1-methylethyl)-1H-pyrazole-5-carboxylate (0.15 g) and Selectfluor™ (0.38 g) followed by acetonitrile (3 ml) and acetic acid (1 ml). The mixture was heated at 100° C. under microwave irradiation for 180 min. Selectfluor™ (0.076 g) was added and the mixture heated at 100° C. under microwave irradiation for 60 min. Further Selectfluor™ (0.15 g) was added and the mixture heated at 100° C. under microwave irradiation for 60 min. Further Selectfluor (0.38 g) was added and the mixture heated at 100° C. under microwave irradiation for 60 min. The solvent was removed in vacuo and the residue was partitioned between DCM (15 ml) and water (15 ml) and separated using a hydrophobic frit. The aqueous layer was extracted with dichloromethane (2×5 ml) and the combined organic layers were concentrated in vacuo. Purification by chromatography on silica gel (20 g silica cartridge), eluting with a gradient of 0-50% DCM in cyclohexane over 20 minutes gave the title compound (100 mg) as a colourless oil.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08658635B2uspto-grants-2014_02