3,6-Dioxabicyclo[3.1.0]hexane → rac-(3R,4S)-4-(pent-4-en-1-yl)oxolan-3-ol

Temperature

-20 °C

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.

1. temperaturethe reaction mixture was slowly warmed to RT
2. stirringstirred for 15 hours
3. customThe reaction mixture was quenched with NH4Cl(aq.)
4. extractionextracted with Et2O (3×)
5. washThe combined organics were washed with H2O and brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude product was purified on SO2 (gradient elution, 10-100% EtOAc/hexanes)

ORD record

ord-b640634047c443daaed9b6c4559aa7c0

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461107B2