Ethyl formate → 2-Phenyl-2-[4-(4-pyridyl)-2-thiazolyl]acetaldehyde

HRID 4347

Reaktionsgleichung

[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)CCN(C)C.C([Li])CCC.[CH:32](OCC)=[O:33]>O1CCCC1>[C:2]1([CH:1]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)[N:12]=2)[CH:32]=[O:33])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of 2-benzyl-4-(4-pyridyl)thiazole (4.00 g, 0.016 mol) and tetramethylethylenediamine (2.5 mL) in dry tetrahydrofuran (35 mL) at -78° C. under nitrogen atmosphere was added dropwise n-butyl lithium (1.6M in hexane, 11.4 mL). The resulting dark mixture was allowed to stir at -78° C. for 15 minutes, warmed to 0° C. for 2 hours, then cooled to -78° C. Ethyl formate (1.47 mL) was added dropwise and the mixture allowed to stir at -78° C. for 30 minutes then at 0° C. for one hour. The reaction mixture was quenched with methanol, concentrated, and chromatographed over silica gel. Recrystallization from hexane/ethyl acetate afforded 2-phenyl-2-[4-(4-pyridyl)-2-thiazolyl]acetaldehyde (1.76 g, 39%). mp. 163°-164° C.

Aufarbeitung

temperaturewarmed to 0° C. for 2 hours
temperaturecooled to -78° C
stirringto stir at -78° C. for 30 minutes
waitat 0° C. for one hour
customThe reaction mixture was quenched with methanol
concentrationconcentrated
customchromatographed over silica gel
customRecrystallization from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-18b8488c6d344783bff5729349d8b2e5
Quelldatensatz: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04725606

Verknüpfte Notizen

Wird geladen…