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

HRID 2202258Notes

Reaction equation

HRID 2202258 reaction equation
[OH-].[Na+].[C@@H:3]1([C:11]([O:13]CC)=[O:12])[CH2:5][C@H:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7]>CCO>[CH2:9]([O:8][C:6]([C@@H:4]1[CH2:5][C@H:3]1[C:11]([OH:13])=[O:12])=[O:7])[CH3:10]

Participants

4

Reactant 2

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

Product 1

HCID 11535603(1R,2R)-2-(ethoxycarbonyl)cyclopropane-1-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

1N Sodium hydroxide (81 mL, 81.36 mmol) was added to a solution of diethyl trans-cyclopropane-1,2-dicarboxylate (15.15 g, 81.36 mmol) in EtOH (100 mL) at 0° C., and the mixture was stirred at 0° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, 2M hydrochloric acid and NaCl were added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5→100% ethyl acetate/hexane) to give trans-2-(ethoxycarbonyl)cyclopropanecarboxylic acid (11.20 g, 70.8 mmol, 87%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, 2M hydrochloric acid and NaCl
  2. additionwere added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-93f983ef447d46cdb7f1892a54c169da
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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