Реакция #2654

Уравнение реакции

ethyl acetate

acetic anhydride

dimethylaminopyridine

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

→

title compound

Выход 81.0%

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

Выход 81.0%

Растворители

pyridine

Условия реакции

Обработка

1. 1
   Другоеthe reaction overnight
2. 2
   КонцентрированиеConcentrate
3. 3
   Другоеthe reaction under vacuum
4. 4
   ПромывкаWash with 0.5M hydrochloric acid that
5. 5
   Сушкаdry over anhydrous magnesium sulfate
6. 6
   Фильтрацияfilter
7. 7
   Концентрированиеconcentrate under vacuum
8. 8
   ДругоеPurify the residue by chromatography (silica gel, 10 g, 1.5×4 cm columnar 20% ethyl acetate/hexane)

Методика

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%).

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