Hydrochloric Acid → 4-[4-(5-Trifluoromethylpyridin-2-yloxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione

HRID 512580Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[CH:10]1[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[O:13][C:12]([CH3:20])([CH3:19])[C:11]1=[O:21])[CH3:2].F[C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.ClCCl>[F:30][C:29]([F:32])([F:31])[C:26]1[CH:27]=[CH:28][C:23]([O:9][C:7]2[CH:6]=[CH:5][C:4]([CH:10]3[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[O:13][C:12]([CH3:20])([CH3:19])[C:11]3=[O:21])=[C:3]([CH2:1][CH3:2])[CH:8]=2)=[N:24][CH:25]=1

Participants

Conditions

Temperature: 140 °C

Procedure

4-(2-Ethyl-4-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (0.100 g, 0.34 mmol) is added to a mixture of 2-fluoro-5-trifluoromethylpyridine (0.061 g, 0.41 mmol) and potassium carbonate (0.110 g, 0.69 mmol) in N,N-dimethylformamide (2 ml), and the mixture is heated at 140° C. under microwave irradiation for 1 hour. The mixture is cooled to room temperature, then acidified by addition of 2M aqueous hydrochloric acid. The mixture is diluted with dichloromethane and passed through a phase separation cartridge. The organic phase is concentrated to around 2 ml, and purified by preparative reverse phase HPLC to give 4-[4-(5-trifluoromethylpyridin-2-yloxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione.

Workup

temperatureThe mixture is cooled to room temperature
custompassed through a phase separation cartridge
concentrationThe organic phase is concentrated to around 2 ml
custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-ea5614788b924a4494e5d354af22685f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102642B2

Reaction notes

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