Reaktion #2647

Reaktionsgleichung

(-)-acetic acid 4-tert-butyldimethylsilyloxy-cyclopent-2-enyl ester

lithium hydroxide monohydrate

water

→

title compound

Ausbeute 92.0%

(+)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol

Ausbeute 92.0%

Lösungsmittel

THF methanol water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONdilute
2. 2
   Extraktionextract with tert-butyl methyl ether
3. 3
   Trocknendry over anhydrous magnesium sulfate
4. 4
   Filtrationfilter
5. 5
   Einengenconcentrate under vacuum
6. 6
   SonstigePurify the residue by flash chromatography (silica gel, 20% ethyl acetate/hexane)

Vorschrift

Dissolve (-)-acetic acid 4-tert-butyldimethylsilyloxy-cyclopent-2-enyl ester (2.3 mmol, prepared in example 10) in THF/methanol/water (2.7/0.9/0.9 mL). Add lithium hydroxide monohydrate (2.5 mmol) with stirring. After stirring for about 3 hours at room temperature, dilute the reaction with water (10 mL) and extract with tert-butyl methyl ether. Combine the organic phases, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 20% ethyl acetate/hexane) to provide the title compound (452 mg, 92% yield) [α]20D =+21.8°, (c=1.02, chloroform).

Quelle