Hydrochloric Acid → 5-(3,3-Dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxylic acid

HRID 1478171Notes

Reaction equation

HRID 1478171 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]#[C:4][C:5]1[O:9][N:8]=[C:7]([C:10]([O:12]CC)=[O:11])[C:6]=1[CH3:15].[OH-].[Na+].Cl.O>C1COCC1.CO>[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]#[C:4][C:5]1[O:9][N:8]=[C:7]([C:10]([OH:12])=[O:11])[C:6]=1[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 118511143Ethyl 5-(3,3-dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxylate

Product 1

HCID 1185111525-(3,3-Dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(3,3-dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxylate (101 mg, 0.429 mmol) in THF (3 mL) and MeOH (1.800 mL) was treated at room temperature with 2M NaOH (aq) (0.429 mL, 0.859 mmol) for 1 hour. 2M HCl (aq) (0.6 mL) and water were added and the aqueous was extracted with EtOAc. The combined organic extracts were dried over MgSO4 and filtered. The solvent was removed under reduced pressure to afford the title compound;

Workup

  1. extractionthe aqueous was extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-481118f6d8f64858b603f28fe0e34274
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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