Sodium Chloride → Diethyl 3,4-pyrroledicarboxylate

HRID 495880Notes

Reaction equation

HRID 495880 reaction equation
S([CH2:11][N+:12]#[C-:13])(C1C=CC(C)=CC=1)(=O)=O.[C:14]([O:23][CH2:24][CH3:25])(=[O:22])/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18].CC(C)([O-])C.[K+].[Na+].[Cl-]>C1COCC1>[NH:12]1[CH:13]=[C:15]([C:14]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 161915Tosylmethyl isocyanideHCID 638144Diethyl fumarateHCID 23665647Potassium tert-butoxide

Product 1

HCID 688199Diethyl 3,4-pyrroledicarboxylateYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tosylmethyl isocyanide (9.8 g, 50 mmol), diethyl fumarate (8.2 mL. 50 mmol.) and dry THF (1000 mL) were added dropwise to a stirred suspension of potassium t-butoxide (11.2 g, 100 mmol) and THF (150 mL). The mixture was stirred for 2 hours, saturated NaCl (500 mL) was added, and the mixture was extracted with THF (2×250 mL). The organic layers were dried (Na2SO4), filtered and concentrated in vacuo to give a solid. The solid was recrystallized from MeOH to give the title compound 4.6 g (44%) (mp 148-149° C.). 1H NMR (DMSO) δ 1.22 (t, 3H, CH3), 4.18 (q, 2H, CH2), 7.39 (s, 2H, ArH), 11.8 (bs, 1H, NH)

Workup

  1. extractionthe mixture was extracted with THF (2×250 mL)
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a solid
  6. customThe solid was recrystallized from MeOH

Sources & evidence

ORD record
ord-e4c8d93d513f4cfe9ecbcfe2427780b8
Source dataset
uspto-grants-2005_09
Patent number
US06942966B1

Reaction notes

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