Ethanol → 5,6-Dihydroxyhexahydro-4,7-methano-2-benzofuran-1(3H)-one

Temperature

-40 °C

Initially, 21.7 g (120 mmol) of 4-oxatricyclo[5.2.1.02, 6]dec-8-en-3-one [Compound (A)] was placed in a 1-L reactor equipped with a stirrer, a thermometer, a cooling tube, and a dropping funnel, was dissolved in 318 g of ethanol and was cooled to −40° C. in a Dewar bath. Separately, 19.0 g (120 mmol) of potassium permanganate (KMnO4) and 14.4 g (120 mmol) of magnesium sulfate (MgSO4) were dissolved in water heated at 60° C., and the resulting solution was added dropwise into the reactor. After the completion of the addition, the reactor was taken out from the Dewar bath, the mixture was left stand to room temperature and was aged over night. After the completion of the reaction, the reaction mixture was filtrated, the filtrate was concentrated, the concentrate was filtrated again to remove insoluble matters, and the filtrate was extracted with ethyl acetate (n=5, s/f=2/1). The ethyl acetate layer was concentrated, the deposited solid matter was washed with toluene, was filtrated, was dried and thereby yielded the title compound [Compound (E)] in a yield of 41%.

1. customequipped with a stirrer
2. temperatureheated at 60° C.
3. additionthe resulting solution was added dropwise into the reactor
4. additionAfter the completion of the addition
5. waitthe mixture was left stand to room temperature
6. waitwas aged over night
7. customAfter the completion of the reaction
8. filtrationthe reaction mixture was filtrated
9. concentrationthe filtrate was concentrated
10. filtrationthe concentrate was filtrated again
11. customto remove insoluble matters
12. extractionthe filtrate was extracted with ethyl acetate (n=5, s/f=2/1)
13. concentrationThe ethyl acetate layer was concentrated
14. washthe deposited solid matter was washed with toluene
15. filtrationwas filtrated
16. customwas dried

ORD record

ord-3175ed16a4894256b344db2a34003a6c

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105268B2