Water → 2-(6-hydroxyhexyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1449432

반응식

HRID 1449432 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K].C(OCC)(=O)C.O>CN(C)C=O>[OH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:13]1[C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]2[C:9]1=[O:19]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 779706-Bromo-1-hexanolHCID 24194345Phthalimide potassium salt

생성물 1

HCID 129502192-(6-hydroxyhexyl)-2,3-dihydro-1H-isoindole-1,3-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-Bromohexan-1-ol (8 g, 44 mmol) and potassium phthalimide (16.4 g, 88 mmol) were heated at 90° C. for two hours in dry N,N-dimethylformamide (50 ml). The mixture was cooled and partitioned between chloroform (150 ml) and water (150 ml). The organic layer washed with water (2×150 ml), dried over anhydrous magnesium sulphate, filtered, and the filtrate evaporated under reduced pressure to give a yellow liquid. The liquid was left at 4° C. for 72 hours before repartitioning between ethyl acetate (150 ml) and water (150 ml). The organic layer was washed with water (2×150 ml), dried over anhydrous magnesium sulphate, filtered, and the filtrate evaporated under reduced pressure. Diethyl ether was added and following cooling the solid was removed by filtration. The process was repeated and the liquors were evaporated to give N-(6-hydroxyhexyl)-phthalimide. 1H-NMR: (60 MHz) (CDCl3), δ 7.7 (4H,s), 3.6 (5H,m) and 1.4 (8H,m) ppm

후처리

  1. temperatureThe mixture was cooled
  2. custompartitioned between chloroform (150 ml) and water (150 ml)
  3. washThe organic layer washed with water (2×150 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customto give a yellow liquid
  8. washThe organic layer was washed with water (2×150 ml)
  9. dry with materialdried over anhydrous magnesium sulphate
  10. filtrationfiltered
  11. customthe filtrate evaporated under reduced pressure
  12. additionDiethyl ether was added
  13. temperaturefollowing cooling the solid
  14. customwas removed by filtration
  15. customthe liquors were evaporated

출처 및 근거

ORD 기록
ord-7dbf8d863d50477e9ebbd5cc579ec244
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599587

연결된 노트

불러오는 중…