2,2-Dimethyl-5-[2-(2,4,5-trifluoro-phenyl)-acetyl]-[1,3]dioxane-4,6-dione → ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate

HRID 1896089Notes

Reaction equation

[CH3:1][C:2]1(C)OC(=O)[CH:5]([C:9](=[O:20])[CH2:10][C:11]2[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=2[F:19])[C:4](=[O:21])[O:3]1>C(O)C>[O:20]=[C:9]([CH2:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[F:19])[CH2:5][C:4]([O:3][CH2:2][CH3:1])=[O:21]

Participants

Conditions

Temperature: 70 °C

Procedure

2,2-Dimethyl-5-[2-(2,4,5-trifluoro-phenyl)-acetyl]-[1,3]dioxane-4,6-dione 1b (15.72 g, 49.6 mmol) was dissolved in 280 mL of ethanol under stirring, then the reaction mixture was heated to 70° C. in an oil bath for 12 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with system B as eluant to obtain the title compound ethyl 3-oxo-4-(2,4,5-trifluoro-phenyl)-butyrate 1c (12 g, yield 88%) as a yellow oil. MS m/z (ESI): 259 [M−1].

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography with system B as eluant

Sources & evidence

ORD record: ord-7af4e37a63de4c11a1e785380e0dc708
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518946B2

Reaction notes

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