4-[2-Methoxyethenyl]-1-phenylbicyclo[2.2.2]octane → Methyl (4-phenylbicyclo[2.2.2]oct-1-yl)acetate

To a stirred solution of 4-[2-methoxyethenyl]-1-phenylbicyclo[2.2.2]octane (Intermediate 7; 12.6 g, 51.99 mmol) in DCM (200 mL) was added pyridinium chlorochromate (33.6 g, 155.97 mmol) in portions and the reaction mixture was allowed to stir at ambient temperature for 2 hrs. Further pyridinium chlorochromate (12 g, 55.99 mmol) was added and stirring was continued for a further 1 hr. The mixture was filtered and the filtrate was concentrated under reduced pressure, ether (200 mL) was added and the organic phase was washed with water (200 mL). Water (200 mL) and ether (2×200 mL) were added to the filtered solid and the mixture was filtered through a pad of celite. The organic extracts were combined, dried (MgSO4) and concentrated to leave a brown gum. This was purified on a 330 g Crawford silica cartridge, loading the sample in DCM and eluting with 5-10-20% EtOAc-isohexane to provide the title compound as a cream solid (7.89 g, 30.53 mmol, 59%); 1H NMR (CDCl3) δ 1.63-1.71 (6H, m), 1.83-1.93 (6H, m), 2.17 (2H, s), 3.67 (3H, s), 7.14-7.19 (1H, m), 7.29-7.32 (4H, m); GC-MS EI m/e M+ 258.

1. stirringstirring
2. waitwas continued for a further 1 hr
3. filtrationThe mixture was filtered
4. concentrationthe filtrate was concentrated under reduced pressure, ether (200 mL)
5. additionwas added
6. washthe organic phase was washed with water (200 mL)
7. additionWater (200 mL) and ether (2×200 mL) were added to the filtered solid
8. filtrationthe mixture was filtered through a pad of celite
9. dry with materialdried (MgSO4)
10. concentrationconcentrated
11. customto leave a brown gum
12. customThis was purified on a 330 g Crawford silica cartridge
13. washeluting with 5-10-20% EtOAc-isohexane

ORD record

ord-a49d12e87c9642f694adccc274cf9346

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017603B2