2,6-Lutidine → (7a-Methyl-1,5-dioxo-octahydro-inden-4-yloxy)-acetaldehyde

A commercial 4% w/w solution of osmium tetraoxide (10 mL, 0.82 mmol, 0.005 eq) was added to a stirred mixture of 4-allyloxy-7a-methyl-hexahydro-indene-1,5-dione (36.4 g, 164 mmol), 2,6-lutidine (57.2 mL, 246 mmol, 1.5 eq) and sodium periodate (210.6 g, 492 mmol, 3 eq) in dioxane (900 mL) and water (300 mL) at 0° C. The reaction mixture was then allowed to warm slowly to room temperature, and stirred for 24 h. The reaction mixture was cooled to 0° C., and then filtered through a fritted funnel. DCM (1 L) was used to wash to salt cake, and the filtrate was used to extract the separated aqueous solution (4×250 mL). The combined organic layer was dried with magnesium sulfate. The resulting mixture was filtered, condensed and the resulting residue purified by flash chromatography using 20-90% ethyl acetate in hexane yield the title compound as a light yellow foam.

1. temperatureThe reaction mixture was cooled to 0° C.
2. filtrationfiltered through a fritted funnel
3. washto wash to salt cake
4. extractionto extract the separated aqueous solution (4×250 mL)
5. dry with materialThe combined organic layer was dried with magnesium sulfate
6. filtrationThe resulting mixture was filtered
7. customcondensed
8. customthe resulting residue purified by flash chromatography

ORD record

ord-132bd8ebdaa34940ad59cac16ebed7f0

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763648B2