4-Fluorobenzophenone → 1-(4-Fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)-1-phenylethanol

HRID 974501

Reaktionsgleichung

[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][N:4]=[N:3]1.C([Li])CCC.[F:13][C:14]1[CH:27]=[CH:26][C:17]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])=[CH:16][CH:15]=1>C1COCC1.CCCCCC>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([OH:19])[CH2:7][C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)=[CH:26][CH:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

A solution of 1,5-dimethyltetrazole (29.25 g; 0.298 mole) in dry THF (400 mL) was cooled to -78° C. and treated with n-butyllithium (133 mL of a 2.5M solution in hexane; 0.3325 mole) over 30 minutes. The mixture was stirred at -78° C. for 30 minutes and treated with 4-fluorobenzophenone (50 g, 0.25 mole. The mixture was stirred at -78° C. for 30 minutes and allowed to warm up to 23° C. over 2 hours. The reaction was quenched with 2N HCl (100 mL) and the organic solvent was removed by evaporation. The residue was extracted with CHCl3 (2×100 mL) and the combined organic layers were dried (Na2SO4) and evaporated to afford a brown oil. Purification by chromatography using 20% EtOAc-hexane as eluent afforded the title compound as a white solid (46.3 g; 62%). m.p.=113°-114° C. (crystallized from EtOAc-hexane). MS (CI): m/e=299 for (M+H)+ ;

Aufarbeitung

stirringThe mixture was stirred at -78° C. for 30 minutes
temperatureto warm up to 23° C. over 2 hours
customThe reaction was quenched with 2N HCl (100 mL)
customthe organic solvent was removed by evaporation
extractionThe residue was extracted with CHCl3 (2×100 mL)
dry with materialthe combined organic layers were dried (Na2SO4)
customevaporated
customto afford a brown oil
customPurification by chromatography

Quellen und Nachweise

ORD-Eintrag: ord-cc3cde0bbb62497c868a9e9b7f8d26aa
Quelldatensatz: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05068346

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