ethyl (1S,2S)-2-phenylcyclopropane-1-carboxylate → 2-Phenyl-1-cyclopropanecarboxylic acid, (1S-trans)-

HRID 1774006Notes

Reaction equation

HRID 1774006 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])C>C1COCC1.CCO.[OH-].[Na+]>[C:9]1([C@H:7]2[CH2:8][C@@H:6]2[C:4]([OH:5])=[O:3])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 1

HCID 816742ethyl (1S,2S)-2-phenylcyclopropane-1-carboxylate

Product 1

HCID 7785172-Phenyl-1-cyclopropanecarboxylic acid, (1S-trans)-

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (1S,2S)-2-phenyl-cyclopropanecarboxylic acid ethyl ester (42 mg, 0.22 mmol, 1.0 eq.) in THF (0.68 mL) and EtOH (0.18 mL), 1M aq. NaOH (0.32 ml) was added. The solution was stirred at r.t. for 18 hours. The organic solvents were removed in vacuo. The residue was diluted with water and washed with AcOEt. The aq. phase was acidified with 2N aq. HCl soln. The mixture was extracted with DCM (3×). The comb. org. phases were dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a colorless oil. The product was used without further purification.

Workup

  1. customThe organic solvents were removed in vacuo
  2. additionThe residue was diluted with water
  3. washwashed with AcOEt
  4. extractionThe mixture was extracted with DCM (3×)
  5. dry with materialphases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03ac03c75fd7456aa437cfdbb5aef52b
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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