Ethyl Acetoacetate → HCID 67313979, compound

HRID 1011976Notes

Reaction equation

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.C([O-])C.[Na+].[F:14][C:15]([F:33])([F:32])[C:16]1[CH:17]=[C:18]([NH:22][N:23]=[C:24](Br)[C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH:19]=[CH:20][CH:21]=1>C(O)C>[CH2:8]([O:7][C:1]([C:2]1[C:24]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[N:23][N:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([F:33])([F:14])[F:32])[CH:17]=2)[C:3]=1[CH3:5])=[O:6])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

An ice cooled solution of ethyl acetoacetate (0.21 ml, 1.63 mmol) in 10 ml ethanol was treated with a solution of sodium ethanolate 21% (in ethanol, 0.6 ml, 1.63 mmol). The reaction mixture was stirred 1 h at 0° C., then N-[3-(trifluoromethyl)phenyl]pyridine-4-carbohydrazonoyl bromide (562 mg, 1.63 mmol) in 5 ml ethanol was added drop wise. The yellow suspension was stirred 1 h at room temperature and 2 days at 50° C. The reaction mixture was concentrated in vacuo and the residual product partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The organic phases were dried over magnesium sulfate and evaporated. Column chromatography (EtOAc:n-heptane 1:1) gave the title compound as a light brown oil (130 mg, 21%). MS: 376.5 (MH+).

Workup

stirringThe yellow suspension was stirred 1 h at room temperature and 2 days at 50° C
concentrationThe reaction mixture was concentrated in vacuo
customthe residual product partitioned between EtOAc and water
extractionThe aqueous layer was extracted with EtOAc
dry with materialThe organic phases were dried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-03421ef5766a439daca3783a764bddfe
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977358B2

Reaction notes

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