Water → 5,6-Dichloro-2-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)isoindoline

HRID 2211716노트

반응식

HRID 2211716 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[Cl:21])[C:17](=O)[N:16]([C:23]1[C:24]([CH3:42])=[C:25]([CH3:41])[C:26]3[O:30][C:29]([CH3:32])([CH3:31])[CH:28]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]=3[C:39]=1[CH3:40])[C:15]2=O.O>O1CCCC1>[Cl:21][C:20]1[CH:19]=[C:18]2[C:14](=[CH:13][C:12]=1[Cl:11])[CH2:15][N:16]([C:23]1[C:24]([CH3:42])=[C:25]([CH3:41])[C:26]3[O:30][C:29]([CH3:31])([CH3:32])[CH:28]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:27]=3[C:39]=1[CH3:40])[CH2:17]2

참가 물질

6

반응물 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 219613375,6-Dichloro-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 155165595,6-Dichloro-2-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)isoindoline수율 18%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of aluminum chloride (1.01 g, 7.59 mmol) in tetrahydrofuran (30 ml) was added lithium aluminum hydride (276.5 mg, 7.29 mmol) and the resulting mixture was stirred for 10 minutes. To this mixture was added a solution of 5,6-dichloro-2-[2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl]-1H-isoindole-1,3(2H)-dione (907.4 mg, 1.89 mmol) in tetrahydrofuran (10 ml) and the resulting mixture was refluxed with heating for 2 hours. The reaction mixture was cooled down to room temperature and water was added into the mixture. The product was extracted twice with ethyl acetate. The combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain 153 mg (18% yield) of the title compound. Melting point: 194-196° C.

후처리

  1. temperaturethe resulting mixture was refluxed
  2. temperaturewith heating for 2 hours
  3. extractionThe product was extracted twice with ethyl acetate
  4. washThe combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-bd3fc75b2cd54f90b225c018431c5a62
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101867B2

반응 노트

불러오는 중…