Potassium Hydroxide → HCID 178491479, compound

HRID 1838635Notes

Reaction equation

HRID 1838635 reaction equation
[OH:1][C:2]1[C:3]([O:27][CH3:28])(C(OC)=O)[CH2:4][CH:5]([CH3:22])[C:6](=[O:21])[C:7]=1[C:8]([C:10]1[C:11]([CH3:20])=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=1)=[O:9].[OH-].[K+]>O1CCOCC1.O>[OH:1][C:2]1[CH:3]([O:27][CH3:28])[CH2:4][CH:5]([CH3:22])[C:6](=[O:21])[C:7]=1[C:8]([C:10]1[C:11]([CH3:20])=[N:12][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:14][CH:15]=1)=[O:9]

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

1.4 g of methyl 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-4-oxocyclohex-2-enecarboxylate in dioxane/water (5:3) are treated with 0.586 g of potassium hydroxide and the mixture is stirred for 3 hours. The mixture is then acidified (pH 3) and extracted with fresh ethyl acetate. The crude product is purified by chromatography analogously to Example H4. 3-Hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)cyclohex-2-enone is obtained as a viscous oil (according to 1H-NMR as a mixture of 3 tautomeric forms).

Workup

  1. extractionextracted with fresh ethyl acetate

Sources & evidence

ORD record
ord-993e12e24eda4b64b968149dfc7acca0
Source dataset
uspto-grants-2004_01
Patent number
US06673938B1

Reaction notes

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