Reaktion #1342686

Reaktionsgleichung

bromo(pent-4-en-1-yl)magnesium

3,6-Dioxabicyclo[3.1.0]hexane

→

Trans-4-pent-4-en-1-yltetrahydrofuran-3-ol

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was slowly warmed to RT
2. 2
   workup.STIRRINGstirred for 15 hours
3. 3
   SonstigeThe reaction mixture was quenched with NH4Cl(aq.)
4. 4
   Extraktionextracted with Et2O (3×)
5. 5
   WaschenThe combined organics were washed with H2O and brine
6. 6
   Trocknendried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe crude product was purified on SO2 (gradient elution, 10-100% EtOAc/hexanes)

Vorschrift

To a mixture of CuI (1.66 g, 8.71 mmol) in THF (100 mL) at −5° C., a 0.5M solution of bromo(pent-4-en-1-yl)magnesium (116 mL, 5.81 mmol) was added. The solution was stirred for 1 hour and cooled to −20° C. 3,6-Dioxabicyclo[3.1.0]hexane (5.0 g, 58.1 mmol) was added dropwise, and the reaction mixture was slowly warmed to RT and stirred for 15 hours. The reaction mixture was quenched with NH4Cl(aq.) and extracted with Et2O (3×). The combined organics were washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The crude product was purified on SO2 (gradient elution, 10-100% EtOAc/hexanes). 1H NMR (500 MHz, CDCl3) δ 5.83-5.75 (m, 1H); 5.04-4.95 (m, 2H); 4.14-4.07 (m, 3H); 3.85 (m, 1H); 3.70 (m, 1H); 3.44 (m, 1H); 2.07 (m, 3H); 1.45 (m, 3H) ppm.

Quelle