Methanol → 5-Methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

Temperature

60 °C

To a suspension of 10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione (9.97 g, 60 mmol) in methanol (200 ml) is added sodium tetrachloroaurate (597 mg, 1.5 mmol) and the reaction mixture is heated to 60° C. for 7 hours. The reaction mixture is allowed to cool down to room temperature and left to stand overnight. The reaction mixture is concentrated under reduced pressure, dissolved in ethyl acetate (200 ml) and washed with aqueous 2N sodium carbonate (100 ml), followed by saturated brine (100 ml). The organic layer is then dried over magnesium sulphate and concentrated under reduced pressure to give 5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (8.62 g)

1. temperatureto cool down to room temperature
2. waitleft
3. concentrationThe reaction mixture is concentrated under reduced pressure
4. dissolutiondissolved in ethyl acetate (200 ml)
5. washwashed with aqueous 2N sodium carbonate (100 ml)
6. dry with materialThe organic layer is then dried over magnesium sulphate
7. concentrationconcentrated under reduced pressure

ORD record

ord-0037591a615e4fe095b275a6c05ed8ab

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530667B2