Реакция #685987

Уравнение реакции

water

dihydrofuran

propargyl alcohol

N-iodosuccinimide

→

iodoether

Выход 92.0%

Trans-2-(propargyloxy)-3-iodotetrahydrofuran

Выход 92.0%

Растворители

CH2Cl2

CH2Cl2

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   workup.WAITthe stirring was continued for 1 hour
3. 3
   ДругоеThe layers were separated
4. 4
   Экстракцияthe aqueous layer extracted with 2×100 mL of CH2Cl2
5. 5
   ПромывкаThe combined organic extracts were washed with a brine solution
6. 6
   workup.ADDITIONcontaining a small amount of sodium thiosulfate (Na2S2O3) (70 mg)
7. 7
   Сушкаdried over anhydrous Na2SO4
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated

Методика

To a stirred, ice cold suspension of 15 g (66.6 mmol) of N-iodosuccinimide in 150 mL of CH2Cl2 was added a mixture of dihydrofuran (66.6 mmol, 4.67 g, 5.1 mL) and propargyl alcohol (100 mmol, 5.0 g, 5.2 mL) in 50 mL of CH2Cl2 over 20 min. After warming to 24° C. with stirring over 2 hours, 200 mL of water was added and the stirring was continued for 1 hour. The layers were separated and the aqueous layer extracted with 2×100 mL of CH2Cl2. The combined organic extracts were washed with a brine solution containing a small amount of sodium thiosulfate (Na2S2O3) (70 mg), dried over anhydrous Na2SO4, filtered, and concentrated. Chromatography over silica gel using 30% EtOAc in hexane yielded (15.4 g, 92%) of iodoether 10 as an oil. 1H-NMR (CDCl3): δ 5.4 (br s, 1H), 4.0-4.3 (m, 5H), 2.7 (m, 1H), 2.48 (br s, 1H), 2.25 (m, 1H); IR (neat), 2956, 2180, 1621, 1440 cm−1.

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