Hydrochloric Acid → 4-Carboxy-5-hexyl-3-(2,6-difluorophenyl)isoxazole

HRID 434041Notes

Reaction equation

HRID 434041 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])=[N:7][O:8][C:9]=1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:4].Cl>CO>[C:3]([C:5]1[C:6]([C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])=[N:7][O:8][C:9]=1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 187562734-Methoxycarbonyl-5-hexyl-3-(2,6-difluorophenyl)isoxazole

Product 1

HCID 187562704-Carboxy-5-hexyl-3-(2,6-difluorophenyl)isoxazoleYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

4-Methoxycarbonyl-5-hexyl-3-(2,6-difluorophenyl)isoxazole (0.30 g, 0.88 mmol) was dissolved in methanol (10 ml), 5N NAOH (1 ml) was added, and the mixture was heated at 50° C. for 2 h. Upon cooling to room temperature, HCl was added until pH 1. Extraction with ethyl acetate and subsequent washing of the organic fraction (brine), drying (MgSO4), filtering, and concentrating afforded the desired 4-carboxy-5-hexyl-3-(2,6-difluorophenyl)isoxazole (0.21 g, 72%) that was used without further purification.

Workup

  1. addition5N NAOH (1 ml) was added
  2. temperatureUpon cooling to room temperature
  3. extractionExtraction with ethyl acetate
  4. washsubsequent washing of the organic fraction (brine)
  5. dry with materialdrying (MgSO4)
  6. filtrationfiltering
  7. concentrationconcentrating

Sources & evidence

ORD record
ord-b7efad12ae4b4bb780affa7107ff99ab
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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