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 221422Notes

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

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 overnight. After cooling, the mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 3-oxo-4-(2,4,5-trifluoro-phenyl)-butyric acid ethyl ester 1c (12 g, yield 88%) as a yellow oil.

Workup

temperatureAfter cooling
concentrationthe mixture was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-f3f34740e6314144a9dd31e5a55dc0d3
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207161B2

Reaction notes

Loading…