Water → (1R,2R)-2-(ethoxycarbonyl)cyclopropane-1-carboxylic acid

HRID 20450Notes

Reaction equation

HRID 20450 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]([C@@H:8]1[CH2:10][C@H:9]1[C:11]([O:13]CC)=[O:12])=[O:7])[CH3:4].O>C(O)C.CC(C)=O>[CH2:3]([O:5][C:6]([C@@H:8]1[CH2:10][C@H:9]1[C:11]([OH:13])=[O:12])=[O:7])[CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 117153031,2-Diethyl (1R,2R)-1,2-cyclopropanedicarboxylate

Product 1

HCID 11535603(1R,2R)-2-(ethoxycarbonyl)cyclopropane-1-carboxylic acidYield 88.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

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%).

Workup

  1. additionPour
  2. extractionextract with ethyl acetate (1×70 mL)
  3. concentrationconcentrate under reduced pressure
  4. filtrationAdd ethyl acetate and filter the resulting slurry
  5. concentrationConcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-59262edff25e4c329021f2b92873c8a4
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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