Methanol → 5-(4-Isopropylcyclohex-1-en-1-yl)-4-methylisoxazole-3-carboxylic acid

HRID 1478148Notes

Reaction equation

HRID 1478148 reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]([O:17]CC)=[O:16])[C:11]=2[CH3:20])=[CH:6][CH2:5]1)([CH3:3])[CH3:2].CO.[OH-].[Na+]>C1COCC1>[CH:1]([CH:4]1[CH2:9][CH2:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]([OH:17])=[O:16])[C:11]=2[CH3:20])=[CH:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 118511103Ethyl 5-(4-isopropylcyclohex-1-en-1-yl)-4-methylisoxazole-3-carboxylate

Product 1

HCID 1185110505-(4-Isopropylcyclohex-1-en-1-yl)-4-methylisoxazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [ethyl 5-(4-isopropylcyclohex-1-en-1-yl)-4-methylisoxazole-3-carboxylate] (92 mg, 0.332 mmol) in THF (5 mL) and MeOH (3 mL) was added 2M sodium hydroxide (aq) (0.166 mL, 0.332 mmol) and the mixture was stirred at room temperature for 2 hrs. The resulting mixture was concentrated under reduced pressure and diluted with water. The aqueous layer was washed with EtOAc, acidified with 2M HCl (aq) and extracted with EtOAc. The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound;

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. washThe aqueous layer was washed with EtOAc
  4. extractionextracted with EtOAc
  5. dry with materialThe organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ddf5f6df394749f9a9c205f9e7a39e57
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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