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

HRID 411861Notes

Reaction equation

HRID 411861 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) 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).

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-7a5c14fb13504cb7981f31b02585e278
Source dataset
uspto-grants-2003_05
Patent number
US06559303B1

Reaction notes

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