반응 #80985

반응 방정식

isobutyramide

1,3-dichloroacetone

NaHCO3

MgSO4

→

desired product

수율 46.0%

4-Chloromethyl-4-hydroxy-2-isopropyloxazoline

수율 46.0%

용매

acetone

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux under argon for 63 hrs
3. 3
   여과vacuum filtered
4. 4
   농축concentrated in vacuo to a dark brown semi-solid
5. 5
   기타The residue was purified by SiO2 flash chromatography

실험 절차

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.

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