Ethyl Acetoacetate → Ethyl 2-(5,6-Diphenyl-1,2,4-triazin-3-yl)acetate

HRID 12564

Reaktionsgleichung

[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5](C)=O.CS(C1[N:17]=[N:18][C:19]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:21]=1)(=O)=O>C1COCC1>[C:22]1([C:20]2[N:21]=[C:5]([CH2:4][C:3]([O:9][CH2:10][CH3:11])=[O:8])[N:17]=[N:18][C:19]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a suspension of NaH (41 mg, 1.61 mmol) in THF (2 ml) at 0° C. was added ethyl acetoacetate (105 mg. 0.80 mmol) dropwise. After the mixture was stirred for 15 min, a solution of 3-(methylsulfonyl)-5,6-diphenyl-1,2,4-triazine (Compound 87) (250 mg, 0.80 mmol) in THF (3 ml) was cannulated into the solution, and the resulting solution was heated to 60° C. for 2 hours. The reaction was then quenched with water. The product was extracted with ethyl acetate. The organic layer was washed with water, and brine, and dried over Na2SO4. The filtered solvent was concentrated in vacuo, and the residue was purified by silica gel chromatography (20% ethyl acetate in hexane) to give title compound as a solid.

Aufarbeitung

customThe reaction was then quenched with water
extractionThe product was extracted with ethyl acetate
washThe organic layer was washed with water, and brine
dry with materialdried over Na2SO4
concentrationThe filtered solvent was concentrated in vacuo
customthe residue was purified by silica gel chromatography (20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag: ord-b001ef4de7204123bc89d9ca3f7063f6
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07728014B2

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