Acetate → 2-[3-(2,6-dimethylphenyl)-2-propenyl]-1H-isoindole-1,3(2H)-dione

HRID 4766

반응식

HRID 4766 반응식
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[CH2:10]([N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])[CH:11]=[CH2:12].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.CCOCC.O>[CH3:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[CH:12]=[CH:11][CH2:10][N:13]1[C:17](=[O:18])[C:16]2[C:15](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]1=[O:23]

참가 물질

8

반응물 4

HCID 175AcetateHCID 11776TriphenylphosphineHCID 684712-Bromo-m-xyleneHCID 224401N-Allylphthalimide

생성물 1

HCID 544475222-[3-(2,6-dimethylphenyl)-2-propenyl]-1H-isoindole-1,3(2H)-dione

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8471Triethylamine용매

반응 조건

온도
100 °C

실험 절차

A mixture 9.3 g (50 mmole) of 2-bromo-m-xylene, 15.0 g (80 mmole) of N-allylphthalimide, 0.56 (2.5 mmole) of paladium acetate and 1.44 (5.5 mmole) of triphenylphosphine were dissolved in 111 ml of triethylamine. The solution was placed in a sealed container and heated at 100° C. for 24 hours. The reaction was then diluted with 800 ml of ether and 200 ml of water. The aqueous layer was separated and the organic washed twice with 100 ml portions of 2N HCl. After filtering the organic phase, washing with saturated KHCO3 and brine, and drying over MgSO4, it was concentrated on the steam bath. The resulting solid product was purified by flash chromotography and used in subsequent reactions.

후처리

  1. customThe aqueous layer was separated
  2. washthe organic washed twice with 100 ml portions of 2N HCl
  3. filtrationAfter filtering the organic phase
  4. washwashing with saturated KHCO3 and brine
  5. dry with materialdrying over MgSO4, it
  6. concentrationwas concentrated on the steam bath
  7. customThe resulting solid product was purified by flash chromotography

출처 및 근거

ORD 기록
ord-adb591f5d8e14cf994f271977a5de703
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04727189

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