反応 #2654

反応方程式

ethyl acetate

acetic anhydride

dimethylaminopyridine

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

→

title compound

収率 81.0%

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

収率 81.0%

溶媒

pyridine

反応条件

後処理

1. 1
   その他the reaction overnight
2. 2
   濃縮Concentrate
3. 3
   その他the reaction under vacuum
4. 4
   洗浄Wash with 0.5M hydrochloric acid that
5. 5
   乾燥dry over anhydrous magnesium sulfate
6. 6
   ろ過filter
7. 7
   濃縮concentrate under vacuum
8. 8
   その他Purify the residue by chromatography (silica gel, 10 g, 1.5×4 cm columnar 20% ethyl acetate/hexane)

実験手順

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%).

出典