Methyl 3-(2,5-dimethoxyphenyl)-2-(3-methoxy-4-(trifluoromethyl)phenyl)-3-oxopropanoate → 1-(2,5-Dimethoxyphenyl)-2-(3-methoxy-4-(trifluoromethyl)phenyl)ethanone

HRID 1522899Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:29])[CH:12]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[C:19]([O:27][CH3:28])[CH:18]=1)C(OC)=O>CCO.Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:29])[CH2:12][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:24])[F:26])=[C:19]([O:27][CH3:28])[CH:18]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of methyl 3-(2,5-dimethoxyphenyl)-2-(3-methoxy-4-(trifluoromethyl)phenyl)-3-oxopropanoate (30.1 g, 73 mmol) in EtOH (400 mL), concentrated HCl (100 mL) was added. The reaction mixture was heated at 130° C. for 3 h, cooled to room temperature, and concentrated. The residue was dissolved in dichloromethane (150 mL) and washed with brine (3×100 mL). The organic layer was dried (Na2SO4), concentrated and purified by silica gel column chromatography (1:10 EtOAc/petroleum ether) to afford the title compound (27.7 g). 1H NMR (DMSO-d6): δ 7.48 (d, 1H), 7.26-7.25 (m, 1H), 7.07-7.03 (m, 1H), 6.93-6.84 (m, 3H), 4.33 (s, 2H), 3.90 (s, 3H), 3.87 (s, 3H), 3.77 (s, 3H).

Workup

temperaturecooled to room temperature
concentrationconcentrated
dissolutionThe residue was dissolved in dichloromethane (150 mL)
washwashed with brine (3×100 mL)
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated
custompurified by silica gel column chromatography (1:10 EtOAc/petroleum ether)

Sources & evidence

ORD record: ord-4b26459ecd784ed682b4c9106deb8609
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09078871B2

Reaction notes

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