1,3-Dichloroacetone → 4-Chloromethyl-4-hydroxy-2-isopropyoxazoline

HRID 1858458노트

반응식

HRID 1858458 반응식
[C:1]([NH2:6])(=[O:5])[CH:2]([CH3:4])[CH3:3].[Cl:7][CH2:8][C:9]([CH2:11]Cl)=[O:10].C([O-])(O)=O.[Na+].[O-]S([O-])(=O)=O.[Mg+2]>CC(C)=O>[Cl:7][CH2:8][C:9]1([OH:10])[CH2:11][O:5][C:1]([CH:2]([CH3:4])[CH3:3])=[N:6]1

참가 물질

6

반응물 4

HCID 107931,3-DichloroacetoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 68424IsobutyramideHCID 516892Sodium Bicarbonate

생성물 1

HCID 107498144-Chloromethyl-4-hydroxy-2-isopropyoxazoline수율 46%

시약·촉매·용매 1

HCID 180Acetone용매

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) δ 1.20-1.28 (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.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux under argon for 63 hrs
  3. filtrationvacuum filtered
  4. concentrationconcentrated in vacuo to a dark brown semi-solid
  5. customThe residue was purified by SiO2 flash chromatography

출처 및 근거

ORD 기록
ord-31712346522f45fca6d05bfcc79036be
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150530

반응 노트

불러오는 중…