Nitrogen → 2-(Cyclopent-3-enyloxy)isoindoline-1,3-dione

HRID 656594노트

반응식

HRID 656594 반응식
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.O[N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.N#N>O>[CH:1]1([O:6][N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:5][CH:4]=[CH:3][CH2:2]1

참가 물질

7

반응물 5

HCID 947NitrogenHCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 2814783-Cyclopenten-1-olHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 197740932-(Cyclopent-3-enyloxy)isoindoline-1,3-dione수율 32.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of cyclopent-3-enol (840 mg, 10.0 mmol) in CH2CT2 (25.0 mL) was added 2-hydroxyisoindolin-1,3-dione (1.96 g, 12.0 mmol) and triphenylphosphine (3.93 g, 15.0 mmol). The resultant mixture was cooled to 0° C. and diisopropylazodicarboxylate (2.95 ml, 15.0 mmol) was slowly added drop wise under N2 atmosphere. The reaction mixture was stirred at ambient temperature for 48 h. To the reaction mixture, H2O (100 mL) was added and extracted with CH2Cl2. The organic layers washed with brine. Dried over anhydrous Na2SO4, filtered and concentrated to provide yellow oil, which was purified by flash chromatography (50% EtOAc-hexane) to yield 2-(cyclopent-3-enyloxy)isoindoline-1,3-dione (740 mg, 32%) as light yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.57-2.87 (m, 4H) 5.12 (t, J=6.19 Hz, 1H) 5.75 (s, 2H) 7.74 (dd, J=5.68, 3.16 Hz, 2H) 7.79-7.87 (m, 2H). MS (ES) [M+H] calculated for C13H12NO3, 230.07. found 230.20.

후처리

  1. extractionextracted with CH2Cl2
  2. washThe organic layers washed with brine
  3. dry with materialDried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide yellow oil, which
  7. customwas purified by flash chromatography (50% EtOAc-hexane)

출처 및 근거

ORD 기록
ord-06777f259a3d4e39a863906af0ddfdfd
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071766B2

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