تفاعل #4984
ord-2754db0450694fd5addb217d80c7651c
معادلة التفاعل
المتفاعلات
الكواشف
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المعالجة
- 1درجة الحرارةafter cooling to 25°
- 2درجة الحرارةThe dark purple reaction mixture was heated in a 50° bath under nitrogen for 20 minutes
- 3درجة الحرارةimmediately cooled in an ice-water bath
- 4ترشيحthe resulting precipitate was collected by filtration
- 5غسيلwashed with cold methanol (2×10 mL)
- 6أخرىVacuum-drying overnight
الإجراء التجريبي
Dideoxyuridine (2.122 g, 10.0 mmol) was dissolved in 30 mL of warm methanol and, after cooling to 25°, iodine monochloride (4.06 g, 25 mmol, 2.5 eq, Fisher) in methanol (20 mL) was added over 5 minutes. The dark purple reaction mixture was heated in a 50° bath under nitrogen for 20 minutes and then immediately cooled in an ice-water bath. After standing without stirring for 165 minutes, the resulting precipitate was collected by filtration and washed with cold methanol (2×10 mL). Vacuum-drying overnight afforded 2.232 g (66%) of iodide 21 as off-white microcrystals. This material was used without further purification in the next reaction, but other preparations were purified by chromatography or recrystallization from boiling methanol (30 mL/g) to give white needles (mp d 160°-164°). NMR indicated that the crude precipitate was homogeneous, but also that the 5'-hydroxyl proton was very broad due to exchange catalyzed by trace impurities. Chromatographed or recrystallized materials afforded spectra in which this proton was, as usual, a sharp triplet.