Hydrochloric Acid → Ethyl 3-(4-hydroxy-3-methylphenyl)-5-isoxazolecarboxylate

HRID 393272Notes

Reaction equation

HRID 393272 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:13][N:12]=2)=[CH:7][C:6]=1[CH3:21].Cl>C1COCC1.CCOC(C)=O>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:13][N:12]=2)=[CH:7][C:6]=1[CH3:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22648868Ethyl 3-[4-(methoxymethoxy)-3-methyl phenyl]-5-isoxazolecarboxylate

Product 1

HCID 136368683Ethyl 3-(4-hydroxy-3-methylphenyl)-5-isoxazolecarboxylateYield 70.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 3-[4-(methoxymethoxy)-3-methylphenyl]-5-isoxazolecarboxylate (725 mg, 2.49 mmol) and aqueous 4 N HCl solution (6 mL) in THF (10 mL) was stirred at 25° C. for 16 h. The reaction mixture was diluted with EtOAc and successively washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound (434 mg, 70% yield) as a yellow solid.

Workup

  1. washsuccessively washed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6022e58c5aa04eae9a3251c8514a04a2
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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