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

HRID 1872343Notes

Reaction equation

HRID 1872343 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
30 °C

Procedure

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) δ 1.24 (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).

Workup

  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

Sources & evidence

ORD record
ord-97b5a92f43704a578a84a09f8510943a
Source dataset
uspto-grants-2000_08
Patent number
US06107482

Reaction notes

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