1,5-Hexadiene → 131719-68-1

Temperature

0 °C

To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 m, 6 H) 1.69 m, 4 H) 1.98 m, 1 H) 3.94 m, 2 H) 5.65 m, 2 H).

1. customquenched with water
2. extractionThe mixture was extracted with diethyl ether
3. washthe diethyl ether layer was washed with saturated sodium bicarbonate solution
4. dry with materialdried with sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-b16a5169c5f34b7e9cc10b6a06cef490

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07378414B2