Ethyl formate → 3,3-Diphenyl-2-(1-methyl-1H-tetrazol-5-yl)propenal

HRID 974504

Reaktionsgleichung

[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][C:9]2[N:13]([CH3:14])[N:12]=[N:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH:26](OCC)=[O:27]>C1COCC1.CCCCCC>[C:15]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:8]([C:9]2[N:13]([CH3:14])[N:12]=[N:11][N:10]=2)[CH:26]=[O:27])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

Reaktionsbedingungen

Temperatur: -7 °C

Versuchsvorschrift

A solution of 2,2-diphenyl-1-(1-methyl-1H-tetrazol-5-yl)-ethene (3.75 g; 14.29 mmole) in dry THF (40 mL) was cooled to -78° C. and treated with n-butyllithium (6.3 mL of a 2.5M soln. in hexane; 15.75 mmole) and the resulting mixture stirred at -7° C. for 30 minutes. Ethyl formate (1.5 mL; 18.58 mmole) was added and the mixture stirred at -78° C. for 2 hour. The reaction was quenched with 2N HCl and the solvent removed by evaporation. The residue was extracted with EtOAc (3×30 mL) and the combined organic layers were dried (MgSO4) and evaporated. The residue was purified by chromatography using 25-35% EtOAc-hexane as eluent to afford starting material (1.35 g; 36%) and the desired title compound (1.65 g; 39%); m.p.=185°-186° C. (crystallized EtOAc-hexane). MS (EI): m/e=290 for M+ ;

Aufarbeitung

stirringthe mixture stirred at -78° C. for 2 hour
customThe reaction was quenched with 2N HCl
customthe solvent removed by evaporation
extractionThe residue was extracted with EtOAc (3×30 mL)
dry with materialthe combined organic layers were dried (MgSO4)
customevaporated
customThe residue was purified by chromatography
customto afford

Quellen und Nachweise

ORD-Eintrag: ord-35c45a27e96e412480c3364caa6c18c4
Quelldatensatz: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05068346

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