Sodium hydride → 1-(Oxan-4-yl)imidazolidin-2-one
Reaktionsgleichung
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:6].[H-].[Na+]>C1COCC1>[O:11]1[CH2:12][CH2:13][CH:8]([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])[CH2:9][CH2:10]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
A dry RB flask charged with 1-(2-chloroethyl)-3-(tetrahydro-2H-pyran-4-yl)urea (19.96 g, 97 mmol) in THF (480 mL), placed under Ar and stirred for 20 minutes at −20° C. after which 60% Sodium Hydride in mineral oil (9.66 g, 241 mmol) was added portion wise. The reaction was allowed to stir at −20° C. for 1 h and was then allowed to warm to ambient temp overnight. The reaction was cooled in an ice bath and quenched via slow addition of saturated NH4Cl (50 mL). Brine (30 mL) was added and the reaction was allowed to stir for 20 minutes. The organic layer was separated and aqueous layer extracted with EtOAc (2×) and THF (2×). The organic layers were combined, dried over anhydrous Na2SO4 and concentrated to dryness to afford a white gummy solid. The crude product was purified by silica gel chromatography (5% MeOH in CH2Cl2) to afford 1-(tetrahydro-2H-pyran-4-yl)imidazolidin-2-one as a white solid (10.54 g, 64% yield, 2 steps). 1H NMR (DMSO-d6): δ 6.24 (s, 1 H), 3.91-3.81 (m, 2 H), 3.73-3.61 (m, 1 H), 3.29-3.23 (m, 2 H), 3.22-3.21 (m, 2 H), 3.19-3.14 (m, 2 H), 1.67-1.53 (m, 2 H), 1.45-1.44 (m, 2 H); MS (ESI) m/z: 171.1 (M+H+).