تفاعل #80985

معادلة التفاعل

isobutyramide

1,3-dichloroacetone

NaHCO3

MgSO4

→

desired product

المردود 46.0%

4-Chloromethyl-4-hydroxy-2-isopropyloxazoline

المردود 46.0%

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةat reflux under argon for 63 hrs
3. 3
   ترشيحvacuum filtered
4. 4
   تركيزconcentrated in vacuo to a dark brown semi-solid
5. 5
   أخرىThe residue was purified by SiO2 flash chromatography

الإجراء التجريبي

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.

المصدر