1-Bromo-3-chloropropane → 1-(3-Chloropropyl)-3,3-dimethylindolin-2-one

HRID 2362970노트

반응식

HRID 2362970 반응식
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][Cl:19]>CN(C)C=O>[Cl:19][CH2:18][CH2:17][CH2:16][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:12])([CH3:1])[C:3]1=[O:11]

참가 물질

5

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-one

생성물 1

HCID 580466771-(3-Chloropropyl)-3,3-dimethylindolin-2-one수율 87.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3,3-dimethylindolin-2-one (1.843 g, 11.43 mmol, 1 equiv) in N,N-dimethylformamide was cooled to 0° C. Sodium hydride (60% dispersion) (503 mg, 12.58 mmol, 1.1 equiv) was slowly added and the reaction was stirred as such until all bubbling had stopped. 1-bromo-3-chloropropane (3.37 ml, 34.3 mmol, 3 equiv) was added to the reaction mixture in one portion. The reaction was allowed to warm to ambient temperature and stirred as such for 16 h. The crude mixture was partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered, concentrated, and the residue was purified using the Biotage flash chromatography system (SNAP 50 g cartridge, Rf=0.5, gradient—5%-30% ethyl acetate in hexanes) to afford the title compound as a light orange oil (2.38 g, 87%); 1H NMR (400 MHz, DMSO-d6): δ 1.26 (s, 6H); 1.98-2.14 (m, 2H); 3.65 (t, 2H, J=6 and 6.8 Hz); 3.77-3.81 (m, 2H); 7.02-7.07 (m, 2H); 7.24-7.28 (m, 1H); 7.33-7.35 (m, 1H); MS for C13H16ClNO m/z 237.99 (M+H)+.

후처리

  1. stirringstirred as such for 16 h
  2. customThe crude mixture was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified

출처 및 근거

ORD 기록
ord-80d85fa3c8fe4ee6bf61a0fbc0eed294
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691836B2

반응 노트

불러오는 중…