Ethyl 3-(2-fluoro-3,6-dimethoxyphenyl)-2-(3-methoxyphenyl)-3-oxopropanoate → 1-(2-Fluoro-3,6-dimethoxyphenyl)-2-(3-methoxyphenyl)ethanone

HRID 2368937Notes

Reaction equation

[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[C:12](=[O:27])[CH:13]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)C(OCC)=O>CS(C)=O.[Cl-].[Na+].O>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[C:12](=[O:27])[CH2:13][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of ethyl 3-(2-fluoro-3,6-dimethoxyphenyl)-2-(3-methoxyphenyl)-3-oxopropanoate (7.8 g, 20.7 mmol) in DMSO (75 mL) and brine (7.5 mL) was stirred at 150° C. for 5 h. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (1:10 EtOAc/petroleum ether) to give the title compound (3.6 g). 1H NMR (CDCl3): δ 7.24-7.15 (m, 1H), 6.90 (t, 1H), 6.84-6.75 (m, 3H), 6.56 (dd, 1H), 4.08 (s, 2H), 3.82 (s, 3H), 3.77 (s, 3H), 3.76 (s, 3H).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe residue was purified by silica gel column chromatography (1:10 EtOAc/petroleum ether)

Sources & evidence

ORD record: ord-dbc3e6c95078447fa7589f2fe2fab6be
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703810B2

Reaction notes

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