Reaktion #48728

ord-59262edff25e4c329021f2b92873c8a4

Reaktionsgleichung

[Na+].[OH-]
sodium hydroxide
CCOC(=O)[C@@H]1C[C@H]1C(=O)OCC
(+/−)-trans-cyclopropane-1,2-dicarboxylic acid diethyl ester
O
water
→
CCOC(=O)[C@@H]1C[C@H]1C(=O)O
desired compound
Ausbeute 88.7%
CCOC(=O)[C@@H]1C[C@H]1C(=O)O
(+/−)-trans-cyclopropane-1,2-dicarboxylic acid monoethyl ester
Ausbeute 88.7%

Edukte

[Na+].[OH-]
sodium hydroxide
CCOC(=O)[C@@H]1C[C@H]1C(=O)OCC
(+/−)-trans-cyclopropane-1,2-dicarboxylic acid diethyl ester
O
water

Reagenzien

Keine

Lösungsmittel

CCO
ethanol
CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONPour
  2. 2
    Extraktionextract with ethyl acetate (1×70 mL)
  3. 3
    Einengenconcentrate under reduced pressure
  4. 4
    FiltrationAdd ethyl acetate and filter the resulting slurry
  5. 5
    EinengenConcentrate the filtrate under reduced pressure

Vorschrift

Add a solution of 0.709 g (17.72 mmol) sodium hydroxide in 7.38 mL ethanol to a solution of (+/−)-trans-cyclopropane-1,2-dicarboxylic acid diethyl ester (3.00 g, 16.11 mmol) in 36.9 mL acetone. Stir at room temperature for 24 hours. Pour reaction mixture into 100 mL water and extract with ethyl acetate (1×70 mL). Acidify the aqueous layer with 5N HCl and concentrate under reduced pressure. Add ethyl acetate and filter the resulting slurry. Concentrate the filtrate under reduced pressure to provide the desired compound (2.26 g, 88.7%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745438B2uspto-grants-2010_06