Methyl Benzoate → HCID 21677242, compound

To a 9:1 ether/hexanes solution (250 mL) in a 500 mL quartz reaction vessel, was added (Z)-9-oxabicyclo[6.1.0]non-4-ene (1.0 g) and methyl benzoate (1.1 g) sensitizer. No attempt to degas the solution was made. The vessel was irradiated with 254 nm light in a Rayonet RPR-100 UV reactor (Southern New England Ultraviolet Company) under constant stirring. At 30 minute intervals, the irradiation was stopped and the entire solution was passed through a column packed with silver nitrate (10%) impregnated silica. The solution that passes through was then transferred back into the quartz flask and irradiation was continued. After 6 hours the irradiation was stopped and the silica was added to a solution of ammonium hydroxide and stirred for 5 minutes after which ether was added and stirring continued for 5 more minutes. After stirring the ether phase was decanted, washed with water, dried with magnesium sulfate, and evaporated yielding (E)-9-oxabicyclo[6.1.0]non-4-ene (0.4 g, 40% yield). 1HNMR (400 MHz CDCl3): δ 5.8-5.7 (m, 1H), 5.4-5.2 (m, 1H), 2.9-2.7 (m, 2H) 2.5-2.0 (m, 8H).

1. customNo attempt to degas the solution
2. customThe vessel was irradiated with 254 nm light in a Rayonet RPR-100 UV reactor (Southern New England Ultraviolet Company) under constant stirring
3. customthe irradiation
4. customthrough was then transferred back into the quartz flask and irradiation
5. customAfter 6 hours the irradiation
6. additionthe silica was added to a solution of ammonium hydroxide
7. additionwas added
8. stirringstirring
9. stirringAfter stirring the ether phase
10. customwas decanted
11. washwashed with water
12. dry with materialdried with magnesium sulfate
13. customevaporated

ORD record

ord-a24e59e2127d45bbb0eefaed5893d2d5

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08900549B2