Potassium Hydroxide → HCID 178491479, compound

HRID 2180908Notes

Reaction equation

HRID 2180908 reaction equation
[OH-].[K+].COC([C:7]1([O:29][CH3:30])[CH2:12][CH:11]([CH3:13])[C:10](=[O:14])[C:9]([C:15]([C:17]2[C:18]([CH3:27])=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=2)=[O:16])=[C:8]1[OH:28])=O>O1CCOCC1.O>[OH:28][C:8]1[CH:7]([O:29][CH3:30])[CH2:12][CH:11]([CH3:13])[C:10](=[O:14])[C:9]=1[C:15]([C:17]1[C:18]([CH3:27])=[N:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=1)=[O:16]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178499206HCID 178499206, compound

Product 1

HCID 178491479HCID 178491479, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

0.586 g of potassium hydroxide is added to 1.4 g of 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)-4-oxo-cyclohex-2-enecarboxylic acid methyl ester in dioxane/water (5:3) and the batch is stirred for 3 hours. The batch is then acidified (pH 3) and extracted with fresh ethyl acetate. The crude product is purified by chromatography analogously to Example P7. 3-Hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)-cyclohex-2-enone is obtained in the form of a viscous oil (as a mixture of 3 tautomeric forms, according to 1H-NMR).

Workup

  1. extractionextracted with fresh ethyl acetate
  2. customThe crude product is purified by chromatography analogously to Example P7

Sources & evidence

ORD record
ord-e3d38e6bd4d84d44b5b78c3c342f81ab
Source dataset
uspto-grants-2005_05
Patent number
US06890885B2

Reaction notes

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