Sodium Hydroxide → 3-(Ethoxycarbonyl)-5-(1-cyanocyclopentyl)benzoic acid

HRID 2243811Notes

Reaction equation

HRID 2243811 reaction equation
[C:1]([C:3]1([C:8]2[CH:9]=[C:10]([C:19]([O:21]CC)=[O:20])[CH:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[OH-].[Na+]>C1COCC1.CCO>[CH2:17]([O:16][C:14]([C:12]1[CH:11]=[C:10]([CH:9]=[C:8]([C:3]2([C:1]#[N:2])[CH2:7][CH2:6][CH2:5][CH2:4]2)[CH:13]=1)[C:19]([OH:21])=[O:20])=[O:15])[CH3:18]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67318465Diethyl 5-(1-cyanocyclopentyl)benzene-1,3-dioate

Product 1

HCID 673184623-(Ethoxycarbonyl)-5-(1-cyanocyclopentyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of diethyl 5-(1-cyanocyclopentyl)benzene-1,3-dioate (0.33 g, 1.05 mmol) and NaOH (1N in H2O, 0.945 mL, 0.945 mmol) in 5 mL THF and 5 mL EtOH was stirred at rt overnight. The reaction mixture was concentrated, diluted with H2O and extracted with ether. The aqueous phase was made acidic with 1N HCl, extracted with EtOAc and the combined organic layers were washed with brine. Drying and solvent evaporation gave 3-(ethoxycarbonyl)-5-(1-cyanocyclopentyl)benzoic acid. 1H NMR (400 MHz, CD3OD) δ 8.58 (m, 1H), 8.35 (m, 2H), 4.43 (q, J=7.1 Hz, 2H), 2.51 (m, 2H), 2.18 (m, 2H), 2.05 (m, 4H), 1.42 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with ether
  4. extractionextracted with EtOAc
  5. washthe combined organic layers were washed with brine
  6. customDrying
  7. customsolvent evaporation

Sources & evidence

ORD record
ord-481e130ceb9149ecb75d638a60c86022
Source dataset
uspto-grants-2010_03
Patent number
US07678783B2

Reaction notes

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