Reaktion #2309923

Reaktionsgleichung

ethyl (6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylate

sodium hydroxide

→

title compound

(±) (6S)-2-Oxobicyclo[3.1.0]hexane-6-carboxylic acid

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe reaction mixture is washed with tert-butyl methyl ether (1×90 mL)
2. 2
   workup.ADDITIONthe aqueous layer is treated with conc. hydrochloric acid (18 mL)
3. 3
   workup.ADDITIONThe mixture is treated with 15 g of sodium chloride
4. 4
   Waschenby washing with ethyl acetate (3×90 mL)
5. 5
   TrocknenThe combined organic extracts are dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo

Vorschrift

To a solution of crude ethyl (6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylate (30.2 g, 180 mmol, uncorrected) in 30 mL of ethanol at room temperature is added 89 mL (178 mmol) of 2N sodium hydroxide. Upon stirring for 80 minutes, the reaction mixture is washed with tert-butyl methyl ether (1×90 mL) and the aqueous layer is treated with conc. hydrochloric acid (18 mL) to reach a pH=1.0. The mixture is treated with 15 g of sodium chloride followed by washing with ethyl acetate (3×90 mL). The combined organic extracts are dried (Na2SO4), filtered, and concentrated in vacuo to give 23.8 g (94%, uncorrected) of the title compound as an off-white solid.

Quelle