Réaction #2650

Équation de réaction

lithium hydroxide monohydrate

chloroform

(-)-acetic acid cis-4-tert-butyloxy-cyclopent-2-enyl ester

water

→

title compound

Rendement 101.0%

(+)-cis-4-tert-butyloxy-cyclopent-2-enol

Rendement 101.0%

Solvants

THF methanol water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONdilute
2. 2
   Extractionextract with tert-butyl methyl ether
3. 3
   Séchagedry over anhydrous magnesium sulfate
4. 4
   Filtrationfilter
5. 5
   Concentrationconcentrate under vacuum
6. 6
   AutrePurify the residue by flash chromatography (silica gel, 2 g, 40% diethyl ether/hexane, 1.5×2.5 cm column)

Mode opératoire

Dissolve (-)-acetic acid cis-4-tert-butyloxy-cyclopent-2-enyl ester (90 mg, 0.45 mmol, prepared in example 14) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (23.7 mg) with stirring. After stirring for about 2 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, 2 g, 40% diethyl ether/hexane, 1.5×2.5 cm column) to provide the title compound (71 mg, quantitative yield, 76% ee) as a pale yellow oil, [α]20 D =+14.6°, (c=1.03, chloroform).

Source