Hydrochloric Acid → 4-[2-Ethyl-5-(2-fluoro-4-nitrophenoxy)phenyl]-2,2,6,6-tetramethylpyran-3,5-dione

HRID 537682Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[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:22][C:23]1[CH:24]=[C:25]([N+:30]([O-:32])=[O:31])[CH:26]=[CH:27][C:28]=1F.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:28]2[CH:27]=[CH:26][C:25]([N+:30]([O-:32])=[O:31])=[CH:24][C:23]=2[F:22])=[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]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(2-ethyl-5-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (135 mg, 0.47 mmol), 3,4-difluoro-1-nitrobenzene (90 mg, 0.56 mmol), and potassium carbonate (130 mg, 0.94 mmol) in N,N-dimethylformamide (3 ml) is heated to 80° C. for 3 hours. The mixture is cooled to room temperature, poured into 2M aqueous hydrochloric acid and extracted with ethyl acetate. The organic extract is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-[2-ethyl-5-(2-fluoro-4-nitrophenoxy)phenyl]-2,2,6,6-tetramethylpyran-3,5-dione.

Workup

temperatureThe mixture is cooled to room temperature
extractionextracted with ethyl acetate
extractionThe organic extract
dry with materialis dried over anhydrous magnesium sulfate
filtrationfiltered
customthe filtrate is evaporated under reduced pressure
customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-5896f6dd8f414b62a52b5aa1cae6461d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865623B2

Reaction notes

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