Dicyclopentadiene → 3a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoindene-5,6-diol

A slurry of tricyclo[5.2.1.02,6]deca-3,8-diene (26.5 g, 0.2 mol), trimethylamine N-oxide dihydrate (22.3 g, 0.2 mol) and osmium tetroxide (2.5 wt % solution in 2-methyl-2-propanol, 2 □l) in dichloromethane (200 ml) was stirred for 18 h. A further portion of osmium tetroxide (2.5 wt % solution in 2-methyl-2-propanol, ca. 2 □l) was added, water (25 ml) and acetone (50 ml) was added and the reaction mixture was stirred for a further 72 h. Pyridine (0.5 ml) and tetrabutylammonium acetate (0.5 g) were added. Florisil (10 g) and aqueous sodium hydrogensulfite solution was added and the reaction mixture was stirred for 20 min. The reaction mixture was filtered and the product was extracted with dichloromethane (3 times). The combined organic extracts were washed with water, brine and then concentrated to give an oil. The crude oil was purified by flash chromatography eluting with ethyl acetate:hexane (10:90) and then ethyl acetate, to give a waxy solid (6.5 g, 19%).

1. stirringthe reaction mixture was stirred for 20 min
2. filtrationThe reaction mixture was filtered
3. extractionthe product was extracted with dichloromethane (3 times)
4. washThe combined organic extracts were washed with water, brine
5. concentrationconcentrated
6. customto give an oil
7. customThe crude oil was purified by flash chromatography
8. washeluting with ethyl acetate:hexane (10:90)

ORD record

ord-73906d6b0952423691dcef7cb06941fe

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07494992B2