Reacción #170290

Ecuación de reacción

1,3-dihydroxy-12H-benzo[b]xanthen-12-one

K2CO3

epithiochlorohydrin

→

title compound

Rendimiento 20.8%

1-hydroxy-3-(thiiran-2-ylmethoxy)-12H-benzo[b]xanthen-12-one

Rendimiento 20.8%

Disolventes

acetone

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   OtroThe reaction liquid
3. 3
   workup.STIRRINGwas stirred
4. 4
   FiltraciónSolid of the reaction mixture was filtered
5. 5
   Otroremoved
6. 6
   Concentraciónthe filtrate was concentrated under reduced pressure
7. 7
   OtroThe resulting residue was separated
8. 8
   Otropurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v))

Procedimiento

1,3-dihydroxy-12H-benzo[b]xanthen-12-one (0.05 g, 0.18 mmol) synthesized in Step 1 of Example 18, K2CO3 (0.07 g, 0.54 mmol), and anhydrous acetone (18 mL) were charged to a dry round-bottom flask. Under stirring, epithiochlorohydrin (0.07 g, 0.72 mmol) dissolved in anhydrous acetone (2 mL) was added thereto. The reaction liquid was stirred with reflux at a temperature of 55 to 60° C. under a nitrogen atmosphere (overnight). Solid of the reaction mixture was filtered and removed, and the filtrate was concentrated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v)) to give the title compound (13.1 mg, 20.8%) as a yellow solid.

Fuente