Reaktion #658325

Reaktionsgleichung

N-iodosuccinimide

2,5-dihydrofuran

1,3-propanediol dimethoxyethane

→

iodoalcohol

Ausbeute 45.0%

3-((4-Iodotetrahydrofuran-3-yl)oxy)propan-1-ol

Ausbeute 45.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched by addition of sat. aq. Na2SO3
2. 2
   workup.ADDITIONthen diluted with water
3. 3
   ExtraktionThe mixture was extracted with Et2O/EtOAc (1:1)
4. 4
   TrocknenThe combined organic phase was dried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated under reduced pressure
7. 7
   SonstigeThe residue was purified by flash column chromatography on silica gel

Vorschrift

To a solution of freshly distilled 2,5-dihydrofuran (700 mg, 0.740 mL, 10 mmol), in a mixture of dry 1,3-propanediol/dimethoxyethane (1:1, 5 mL) at 0° C. under argon, were successively added NH4OAc (77 mg, 1 mmol), followed by N-iodosuccinimide (11 mmol, 2.47 g). The mixture was warmed to 23° C. and stirred for 12 h protected from light. The reaction was quenched by addition of sat. aq. Na2SO3 then diluted with water. The mixture was extracted with Et2O/EtOAc (1:1). The combined organic phase was dried (Na2SO4), filtered, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel using hexanes/EtOAc (4:1, 3:1 then 2.5:1) to give iodoalcohol 23 (1.2 g, 45%) as a pale yellow oil. TLC: Rf=0.3 (hexanes/EtOAc=1:1); 1H NMR (CDCl3, 400 MHz) δ 4.33 (m, 1H), 4.29-4.19 (m, 3H), 4.04 (dd, J=2.2, 9.8 Hz, 1H), 3.79 (dd, J=1.5, 9.8 Hz, 1H), 3.76-3.69 (m, 3H), 3.60 (m, 1H), 1.81 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 88.2, 76.1, 71.8, 67.9, 60.6, 32.3, 23.4.

Quelle