반응 #2654

반응 방정식

ethyl acetate

acetic anhydride

dimethylaminopyridine

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

→

title compound

수율 81.0%

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

수율 81.0%

용매

pyridine

반응 조건

후처리

1. 1
   기타the reaction overnight
2. 2
   농축Concentrate
3. 3
   기타the reaction under vacuum
4. 4
   세척Wash with 0.5M hydrochloric acid that
5. 5
   건조dry over anhydrous magnesium sulfate
6. 6
   여과filter
7. 7
   농축concentrate under vacuum
8. 8
   기타Purify the residue by chromatography (silica gel, 10 g, 1.5×4 cm columnar 20% ethyl acetate/hexane)

실험 절차

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%).

출처