Potassium Carbonate → Ethyl 3-(4-fluorophenyl)-3-oxo-2-(3-trifluoromethylbenzyl)propionate

HRID 1610267Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 3-(4-fluorophenyl)-3-oxopropionate (10 g, 47.6 mmol), 3-trifluoromethylbenzyl chloride (8.33 g, 42.8 mmol), potassium carbonate (13.2 g, 95.1 mmol) and acetonitrile (200 ml) was stirred at 60° C. for 24 hrs. The reaction solution was concentrated under reduced pressure, water (200 ml) was added, and the mixture was extracted with ethyl acetate (200, 100 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:toluene=1:1-1:2-toluene) to give ethyl 3-(4-fluorophenyl)-3-oxo-2-(3-trifluoromethylbenzyl)propionate (10.2 g, 65%) as an oil.

Workup

concentrationThe reaction solution was concentrated under reduced pressure, water (200 ml)
additionwas added
extractionthe mixture was extracted with ethyl acetate (200, 100 ml)
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:toluene=1:1-1:2-toluene)

Sources & evidence

ORD record: ord-b7fcb49de9c74359a7f00150afc467ce
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982348B2

Reaction notes

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