Sodium Hydroxide → 4-Methyl-5-(6-methyl-3,6-dihydro-2H-pyran-2-yl)isoxazole-3-carboxylic acid

HRID 1478192Notes

Reaction equation

HRID 1478192 reaction equation
[CH3:1][C:2]1[C:3]([C:14]([O:16]CC)=[O:15])=[N:4][O:5][C:6]=1[CH:7]1[CH2:12][CH:11]=[CH:10][CH:9]([CH3:13])[O:8]1.[OH-].[Na+]>CO.C1COCC1>[CH3:1][C:2]1[C:3]([C:14]([OH:16])=[O:15])=[N:4][O:5][C:6]=1[CH:7]1[CH2:12][CH:11]=[CH:10][CH:9]([CH3:13])[O:8]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118511051Ethyl 4-methyl-5-(6-methyl-3,6-dihydro-2H-pyran-2-yl)isoxazole-3-carboxylate

Product 1

HCID 1185110774-Methyl-5-(6-methyl-3,6-dihydro-2H-pyran-2-yl)isoxazole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-methyl-5-(6-methyl-3,6-dihydro-2H-pyran-2-yl)isoxazole-3-carboxylate (14 mg, 0.056 mmol) in MeOH (0.2 mL) and THF (0.3 mL) was added 2M NaOH (aq) (27.9 μl, 0.056 mmol). The reaction mixture was stirred at room temperature for 3 hours. The resulting mixture was concentrated under reduced pressure and 2M NaOH (aq) (1 mL) and water (1 mL) added. The aqueous was extracted with DCM (×3) and the combined organic extracts passed through a phase separating cartridge. The eluent was concentrated under reduced pressure to afford the title compound.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure and 2M NaOH (aq) (1 mL) and water (1 mL)
  2. additionadded
  3. extractionThe aqueous was extracted with DCM (×3)
  4. customseparating cartridge
  5. concentrationThe eluent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-81fb8ac0d89a4bccb5c99bbf164565bc
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

Loading…