HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sulfuric Acid → Ethyl 3-(4-fluorophenyl)-4-methylisoxazole-5-carboxylate

HRID 2388174
Notes
Print preview

Reaction equation

HRID 2388174 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:18][OH:19])[CH:9]([CH3:17])[C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([CH3:17])=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:19][N:18]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 86648116Ethyl 4-(4-fluorophenyl)-4-(hydroxyimino)-3-methyl-2-oxobutanoate

Product 1

HCID 67530024Ethyl 3-(4-fluorophenyl)-4-methylisoxazole-5-carboxylateYield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(4-fluorophenyl)-4-(hydroxyimino)-3-methyl-2-oxobutanoate (10.1 g, 37.8 mmol) and concentrated sulfuric acid (10 mL) were added to 150 mL of absolute ethanol and the mixture was refluxed for 20 hours. After the mixture cooled to room temperature, saturated sodium bicarbonate solution was added to neutralize the mixture. The product was extracted with EtOAc and the combined organic layer was dried over MgSO4 and concentrated to give 8.6 g of the title compound. MS: (+) m/z 250.41 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. extractionThe product was extracted with EtOAc
  3. dry with materialthe combined organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d6586f614a254607bbf92db272de601f
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08269008B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes