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1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → Diallyl 2-[2-(1,3-dioxoisoindolin-2-yl)ethyl]propanedioate

HRID 481574
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 481574
[H-].[Na+].[C:3]([O:12][CH2:13][CH:14]=[CH2:15])(=[O:11])[CH2:4][C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6].Br[CH2:17][CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29]>C1COCC1>[C:20]1(=[O:29])[N:19]([CH2:18][CH2:17][CH:4]([C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6])[C:3]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]12
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Komponenten

5

Edukt 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 24758Sodium hydrideHCID 228227Diallyl malonate

Produkt 1

HCID 22116402Diallyl 2-[2-(1,3-dioxoisoindolin-2-yl)ethyl]propanedioateAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of sodium hydride (4.35 g, 0.18 mol) in freshly distilled THF (100 mL) was cooled to 0° C. and treated with diallyl malonate (35 g, 0.19 mol) over 40 min via a dropping funnel. After stirring at room temperature for 30 min, N-(2-bromoethyl)phthalimide (43.9 g, 0.17 mol) was added to the solution in one portion and the mixture was heated to reflux. After 48 h the solution was cooled to 0° C., quenched with 2N HCl and concentrated to about 20% of its original volume. The concentrate was diluted with ethyl acetate (300 mL) and washed successively with satd. aq. K2CO3 and NaCl. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. Purification by flash column chromatography (5-25% ethyl acetate:hexanes) provided diallyl 2-phthalimidoethylmalonate (41.2 g, 67%) as a colorless oil. 1H NMR (300 MHz, CDCl3) d 7.82 (m, 2H), 7.72 (m, 2H), 5.85 (m, 2H), 5.30 (m, 2H), 5.22 (m, 2H), 4.60 (m, 4H), 3.80 (t, J=6.6 Hz, 2H), 3.46 (t, J=7.2 Hz, 1H), 2.30 (dd, J=13.8, 6.9 Hz, 2H). ##STR222## Step 3

Aufarbeitung

  1. temperaturethe mixture was heated to reflux
  2. temperatureAfter 48 h the solution was cooled to 0° C.
  3. customquenched with 2N HCl
  4. concentrationconcentrated to about 20% of its original volume
  5. additionThe concentrate was diluted with ethyl acetate (300 mL)
  6. washwashed successively with satd
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification by flash column chromatography (5-25% ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ae22c7efff774adc8f67872dc72ce28c
Quelldatensatz
uspto-grants-1998_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05789434

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