1,3-Cyclohexadiene → Bicyclo[2.2.2]oct-5-en-2-one

Temperature

90 °C

A mixture of 7.0 g of α-acetoxyacrylonitrile and 3.2 g of 1,3-cyclohexadiene was heated in a closed microwave tube at 90° C. for 24 h. The obtained brown oil was taken up in DCM and evaporated. The crude mixture was washed over a pad of Celite (2 cm) using 300 mL of Hept-EtOAc (9:1) and then concentrated in vacuo. The yellow oil was redissolved in 10 mL DMSO and 3.2 g of KOH, dissolved in 5 mL water, was carefully added. The resulting black mixture was stirred for 2 d at rt, diluted with water and extracted 3 times with Hept. The combined organic phases were washed 3 times with brine, dried over Na2SO4 and concentrated in vacuo to obtain 1.0 g of rac-(1R*,4R*)-bicyclo[2.2.2]oct-5-en-2-one as beige solid.

1. customevaporated
2. washThe crude mixture was washed over a pad of Celite (2 cm)
3. concentrationconcentrated in vacuo
4. dissolutionThe yellow oil was redissolved in 10 mL DMSO
5. dissolution3.2 g of KOH, dissolved in 5 mL water
6. additionwas carefully added
7. additiondiluted with water
8. extractionextracted 3 times with Hept
9. washThe combined organic phases were washed 3 times with brine
10. dry with materialdried over Na2SO4
11. concentrationconcentrated in vacuo

ORD record

ord-790ee73cd05b4e1e8a7c970a6916e2c1

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202885B2