Toluene → HCID 178477152, compound

Temperature

100 °C

A mixture of 30 g (90 mmol) of trans-2-phenyl-5-(p-toluenesulfonyloxy)-1,3-dioxane (prepared as described in Tetrahedron, 48, 5941-5950), 15.3 g (134 mmol) of potassium thioacetate, 240 ml of toluene and 60 ml of N,N-dimethylacetamide was stirred at 100° C. for 3 hours and then at 110-120° C. for 7 hours. After cooling, the reaction mixture was partitioned between toluene and water. The organic layer was then washed with water, dried over anhydrous magnesium sulfate and concentrated. The resulting oily residue was purified by chromatography on a silica gel (200 g) column using a 1:4 mixture of ethyl acetate and hexane as the eluant to afford the crude title compound as a solid. This solid was recrystallized from a mixture of ethyl acetate and hexane to afford 10 g (yield 47%) of the title compound as brown needle-like crystals.

1. waitat 110-120° C. for 7 hours
2. temperatureAfter cooling
3. customthe reaction mixture was partitioned between toluene and water
4. washThe organic layer was then washed with water
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated
7. customThe resulting oily residue was purified by chromatography on a silica gel (200 g) column
8. additiona 1:4 mixture of ethyl acetate and hexane as the eluant
9. customto afford the crude title compound as a solid
10. customThis solid was recrystallized from a mixture of ethyl acetate and hexane

ORD record

ord-b753cb538541407eb4f3db6fe1c5c801

Source dataset

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06337403B1