Reacción #2654

Ecuación de reacción

ethyl acetate

acetic anhydride

dimethylaminopyridine

(-)-cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enol

→

title compound

Rendimiento 81.0%

(+)-acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester

Rendimiento 81.0%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction overnight
2. 2
   ConcentraciónConcentrate
3. 3
   Otrothe reaction under vacuum
4. 4
   LavadoWash with 0.5M hydrochloric acid that
5. 5
   Secadodry over anhydrous magnesium sulfate
6. 6
   Filtraciónfilter
7. 7
   Concentraciónconcentrate under vacuum
8. 8
   OtroPurify the residue by chromatography (silica gel, 10 g, 1.5×4 cm columnar 20% ethyl acetate/hexane)

Procedimiento

Dissolve (-)-cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enol (292 mg, 1.59 mmol, prepared in example 11) in pyridine (2.8 mL) and treat with acetic anhydride (0.39 mL) and dimethylaminopyridine (16 mg). Stir the reaction overnight. Concentrate the reaction under vacuum, dissolve the residue with ethyl acetate (10 mL). Wash with 0.5M hydrochloric acid that is 1/2 saturated with brine (2×10 mL), saturated sodium bicarbonate (10 mL), brine (10 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by chromatography (silica gel, 10 g, 1.5×4 cm columnar 20% ethyl acetate/hexane) to provide the title compound (290 mg, 81%).

Fuente