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

HRID 899460Notes

Reaction equation

HRID 899460 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-33d045ba826e4acd8481f88baf74cbc6
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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