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

HRID 343767

반응식

HRID 343767 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 22116402Diallyl 2-[2-(1,3-dioxoisoindolin-2-yl)ethyl]propanedioate수율 67.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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-phthalimidoethyl)malonate (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).

후처리

  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)

출처 및 근거

ORD 기록
ord-dad3deae71e941dbbbcf044dd5be67aa
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05863915

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