Tetrahydrofuran → 1-N-Propylphthalimido-1H-pyrrole-3,4-dicarboxylate diethyl ester

HRID 1533470노트

반응식

HRID 1533470 반응식
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:2]1.[H-].[Na+].BrCCC[N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].[CH2:33]1[CH2:37]OC[CH2:34]1>>[CH2:14]([O:13][C:11]([C:3]1[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:5][N:1]([CH2:34][CH2:33][CH3:37])[C:2]=1[N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32])=[O:12])[CH3:15]

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 688199Diethyl 3,4-pyrroledicarboxylate

생성물 1

HCID 697348301-N-Propylphthalimido-1H-pyrrole-3,4-dicarboxylate diethyl ester수율 92%

반응 조건

온도
30 °C

실험 절차

A solution of diethyl pyrrole-3,4-dicarboxylate (39 g, 0.185 mol) in THF (1600 mL) was treated with NaH (60%, 7.6 g, 0.19 mol). The reaction mixture was heated to reflux for 1 hour. The reaction was then cooled to 30° C. and N-(3-bromopropyl)phthalimide (52 g, 0.19 mol) was added. The reaction mixture was heated to reflux for 1 hour, cooled, filtered, and concentrated in vacuo. The resultant gum was partitioned between ETOAC/H2O and extracted with EtOAC (2×300 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The resultant solid was recrystallized from EtOAC to give the title compound 68 g (92%) (mp 100-101° C.). 1H NMR (DMSO) δ1.24 (t, 3H, CH), 2.06 (m, 2H, CH3), 3.57 (t, 2H, CH2), 4.14 (m, 4H, CH2), 7.49 (s, 2H, ArH), 7.86 (m, 4H, ArH)

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 1 hour
  5. temperaturecooled
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant gum was partitioned between ETOAC/H2O
  9. extractionextracted with EtOAC (2×300 mL)
  10. dry with materialThe organic layer was dried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe resultant solid was recrystallized from EtOAC

출처 및 근거

ORD 기록
ord-ebe3117eea7b4e998a60ba06d33a7e04
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06207826B1

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