Phthalimide → 2-(4,4-Dimethylcyclohex-2-enyl)isoindoline-1,3-dione

HRID 2280769노트

반응식

HRID 2280769 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:29])[NH:21]1.[CH3:31][C:32]1([CH3:39])[CH2:37][CH2:36][CH:35](O)[CH:34]=[CH:33]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:31][C:32]1([CH3:39])[CH2:37][CH2:36][CH:35]([N:21]2[C:22](=[O:29])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:20]2=[O:30])[CH:34]=[CH:33]1

참가 물질

6

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5435082-Cyclohexen-1-ol, 4,4-dimethyl-

생성물 1

HCID 709821252-(4,4-Dimethylcyclohex-2-enyl)isoindoline-1,3-dione수율 42.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Resin supported triphenylphosphine (32.7 g, 106 mmol), isoindoline-1,3-dione (17.19 g, 117 mmol), and 4,4-dimethylcyclohex-2-enol (13.4 g, 106 mmol) were combined and THF (197 mL) was added. The mixture was stirred and cooled to 0° C., then diisopropyl azodicarboxylate (21.09 mL, 107 mmol) was added drop-wise over 2 min. The reaction was stirred and allowed to warm slowly to ambient temperature overnight. The reaction mixture was filtered and then concentrated to a yellow solid under reduced pressure. Ethyl acetate (200 mL) was added and the resulting solids were filtered off again. The ethyl acetate filtrate was washed with water (100 mL), the aqueous layer extracted with ethyl acetate (100 mL), the combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated to an oil that was purified by silica gel chromatography (0-20% ethyl acetate/hexane) to afford 2-(4,4-dimethylcyclohex-2-enyl)isoindoline-1,3-dione (11.59 g, 45.4 mmol, 42.8% yield) as an oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.84 (s, 4H), 5.51-5.62 (m, 1H), 5.43 (d, J=10.15 Hz, 1H), 4.59-4.74 (m, 1H), 2.14-2.30 (m, 1H), 1.67-1.81 (m, 1H), 1.44-1.68 (m, 2H), 1.09 (s, 3H), 1.01 (s, 3H); MS (ESI) m/z 256.2 [M+1]+.

후처리

  1. stirringThe reaction was stirred
  2. temperatureto warm slowly to ambient temperature overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated to a yellow solid under reduced pressure
  5. additionEthyl acetate (200 mL) was added
  6. filtrationthe resulting solids were filtered off again
  7. washThe ethyl acetate filtrate was washed with water (100 mL)
  8. extractionthe aqueous layer extracted with ethyl acetate (100 mL)
  9. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated to an oil that
  12. customwas purified by silica gel chromatography (0-20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-6cbb92ec8a99406e8b85e9557196af1f
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139534B2

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