Potassium Carbonate → HCID 22261818, compound

HRID 1610411Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.[F:17][C:18]([F:28])([F:27])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:16])[CH:10]([CH2:23][C:22]2[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:27])[F:28])=[CH:26][CH:25]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 3-(4-methoxyphenyl)-3-oxopropionate (20 g, 84.6 mmol) in acetonitrile (200 ml) were added 4-trifluoromethylbenzyl bromide (20.2 g, 84.6 mmol) and potassium carbonate (23.4 g, 169 mmol) and the mixture was stirred at 60° C. for 2 hrs. The reaction solution was evaporated under reduced pressure, diluted with water (500 ml) and extracted with ethyl acetate (500 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (toluene:hexane=1:1-toluene) to give ethyl 3-(4-methoxyphenyl)-3-oxo-2-((4-(trifluoromethyl)phenyl)methyl)propionate (19.2 g, 56%) as a colorless oil.

Workup

customThe reaction solution was evaporated under reduced pressure
additiondiluted with water (500 ml)
extractionextracted with ethyl acetate (500 ml×2)
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (toluene:hexane=1:1-toluene)

Sources & evidence

ORD record: ord-295077da3af945f4a3937eda96af6c1f
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982348B2

Reaction notes

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