Hydrochloric Acid → Ethyl 2-(4-fluorobenzoyl)-3-oxo-4-phenylbutanoate

HRID 860412

Reaction equation

[Cl-].[Mg+2].[Cl-].[O:4]=[C:5]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.Cl>O1CCCC1.C(OCC)(=O)C.N1C=CC=CC=1>[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([CH:6]([C:5](=[O:4])[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:25])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspensin of magnesium chloride (1.46 g) in tetrahydrofuran (10 ml) was added a solution of ethyl 3-oxo-4-phenylbutanoate (2.0 g) in tetrahydrofuran (10 ml) and the mixture was cooled to 0° C., then pyridine (2.5 ml) was added. The mixture was stirred at 20° C. for 30 minutes, then a solution of 4-fluorobenzoyl chloride (2.44 g) in tetrahydrofuran (10 ml) was added at 0° C. After stirring at 20° C. for 2 hours, the mixure was partitoned between 0.5N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5) to give ethyl 2-(4-fluorobenzoyl)-3-oxo-4-phenylbutanoate (2.15 g) as an oil.

Workup

stirringAfter stirring at 20° C. for 2 hours
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5)

Sources & evidence

ORD record: ord-6e2cc6132f9e4460b2e12f9e04928393
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153854B2

Linked notes

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