Dimethylformamide → 4-Chloro-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21006

반응식

HRID 21006 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([NH:7][C:8]([CH3:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])=[O:6].CN(CCN(C)C)C.C([Li])(CC)C.CCCCCC.CN([CH:42]=[O:43])C>C1COCC1.O>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:4]2[C:3]=1[CH:42]([OH:43])[N:7]([C:8]([CH3:16])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:9])[C:5]2=[O:6]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 474447613-chloro-N-(1-methyl-1-phenylethyl)benzamideHCID 178444656HCID 178444656, 화합물

생성물 1

HCID 684900434-Chloro-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone수율 89%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

3-Chloro-N-(1-methyl-1-phenylethyl)benzamide (7.00 g, 25.6 mmol) was dissolved in THF (280 mL), and the solution was added with TMEDA (12.4 mL, 81.9 mmol), then added with sec-butyllithium-hexane solution (0.99 mol/L, 82.7 mL, 81.9 mmol) by drops at −78° C. for 40 minutes under argon atmosphere, followed by stirring at the same temperature for 2.5 hours. Then, the mixture was added with DMF (4.36 mL, 56.3 mmol) and warmed from −78° C. to room temperature over 2 hours. The reaction mixture was added with water, extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by slurry using diisopropyl ether to obtain 4-chloro-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (6.86 g, yield 89%).

후처리

  1. temperaturewarmed from −78° C. to room temperature over 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by slurry

출처 및 근거

ORD 기록
ord-f45e4ddcaba84c37bb2475ecd5f8e92f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

연결된 노트

불러오는 중…