Potassium Hydroxide → Furo(3,4-b)pyridine-3-carboxylic acid, 1,4,5,7-tetrahydro-2-methyl-5-oxo-4-(2-(trifluoromethyl)phenyl)-, ethyl ester

HRID 371412Notes

Reaction equation

HRID 371412 reaction equation
C(O[CH2:5][C:6](=O)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=O)C.[NH2:14]/[C:15](/[CH3:22])=[CH:16]\[C:17]([O:19][CH2:20][CH3:21])=[O:18].[F:23][C:24]([F:34])([F:33])[C:25]1C=[CH:31][CH:30]=[CH:29][C:26]=1C=O.[OH-].[K+]>C(O)C>[CH3:22][C:15]1[NH:14][C:12]2[CH2:11][O:10][C:8](=[O:9])[C:7]=2[CH:6]([C:5]2[CH:31]=[CH:30][CH:29]=[CH:26][C:25]=2[C:24]([F:34])([F:33])[F:23])[C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 11480907Ethyl 4-acetoxyacetoacetate

Product 1

HCID 3070026Furo(3,4-b)pyridine-3-carboxylic acid, 1,4,5,7-tetrahydro-2-methyl-5-oxo-4-(2-(trifluoromethyl)phenyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50 millimols each of ethyl 4-acetoxy-3-oxo-butyrate, ethyl 3-aminocrotonate and 2-trifluoromethylbenzaldehyde in 100 ml of ethanol were boiled under reflux for 24 hours, 2 g of potassium hydroxide were then added, and the mixture was boiled for a further hour. After the mixture had cooled, the product was precipitated with a water/sodium chloride mixture and was recrystallized from methanol.

Workup

  1. temperatureunder reflux for 24 hours
  2. waitthe mixture was boiled for a further hour
  3. temperatureAfter the mixture had cooled
  4. customthe product was precipitated with a water/sodium chloride mixture
  5. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-c572f6dae9e6410db0705764869a9365
Source dataset
uspto-grants-1985_07
Patent number
US04532248

Reaction notes

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