Hydrochloric Acid → 5-(4,4-Dimethylcyclopent-1-en-1-yl)-4-methylisoxazole-3-carboxylic acid

HRID 1478156Notes

Reaction equation

HRID 1478156 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:6][C:5]([C:7]2[O:11][N:10]=[C:9]([C:12]([O:14]CC)=[O:13])[C:8]=2[CH3:17])=[CH:4][CH2:3]1.[OH-].[Na+].Cl>C(O)C.O>[CH3:1][C:2]1([CH3:18])[CH2:6][C:5]([C:7]2[O:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[C:8]=2[CH3:17])=[CH:4][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118511024Ethyl 5-(4,4-dimethylcyclopent-1-en-1-yl)-4-methylisoxazole-3-carboxylate

Product 1

HCID 1185110675-(4,4-Dimethylcyclopent-1-en-1-yl)-4-methylisoxazole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 5-(4,4-dimethylcyclopent-1-en-1-yl)-4-methylisoxazole-3-carboxylate (243 mg, 0.975 mmol) in ethanol (5 mL), 2M NaOH (aq) (0.975 mL, 1.949 mmol) was added and the solution was stirred at room temperature. Upon completion the reaction mixture was diluted with water (30 mL) and acidified to pH 5-6 by the addition of 2M HCl (aq). The aqueous phase was extracted with EtOAc (2×20 mL) and the combined organic extracts were washed with brine (20 mL), dried over MgSO4 and filtered. The solvent was removed under reduced pressure to afford the title compound;

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  2. washthe combined organic extracts were washed with brine (20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7c5b43916f064715a2ad899a4ee52363
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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