Reaktion #80985

Reaktionsgleichung

isobutyramide

1,3-dichloroacetone

NaHCO3

MgSO4

→

desired product

Ausbeute 46.0%

4-Chloromethyl-4-hydroxy-2-isopropyloxazoline

Ausbeute 46.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturat reflux under argon for 63 hrs
3. 3
   Filtrationvacuum filtered
4. 4
   Einengenconcentrated in vacuo to a dark brown semi-solid
5. 5
   SonstigeThe residue was purified by SiO2 flash chromatography

Vorschrift

To a solution of isobutyramide (9.876 g, 0.1122 mol) in acetone (130 mL) was added 1,3-dichloroacetone (10.0 g, 0.0748 mol), NaHCO3 (9.429 g, 0.1122 mol), and MgSO4 (18.01 g, 0.1496 mol). The mixture was heated at reflux under argon for 63 hrs, then cooled to room temperature, vacuum filtered, and concentrated in vacuo to a dark brown semi-solid. The residue was purified by SiO2 flash chromatography using a gradient of EtOAc/CH2Cl2 (5%, 10%, 20%. 40%) to obtain the desired product as an orange liquid (6.06 g, 0.0341 mol, 46%): 1H NMR (CDCl3) δ1.20-1.28 (m, 6H), 2.56-2.72 (m, 1H), 3.70 (s, 2H), 4.18 (d, J=9.6 Hz, 1H), 4.38 (d, J=9.6 Hz, 1H). Mass spectrum: (M+H)+ =178, 180.

Quelle