Diethyl Ether → Ethyl 3-methyl-1H-pyrrole-2-carboxylate

HRID 1874992Notes

Reaction equation

HRID 1874992 reaction equation
C1CCN2C(=NCCC2)CC1.Cl[C:13]1([CH3:33])[CH2:17][CH2:16][N:15](S(C2C=CC(C)=CC=2)(=O)=O)[C@@H:14]1[C:28]([O:30][CH2:31][CH3:32])=[O:29].C(OCC)C>C1COCC1>[CH3:33][C:13]1[CH:17]=[CH:16][NH:15][C:14]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68485567HCID 68485567, compound

Product 1

HCID 5324582Ethyl 3-methyl-1H-pyrrole-2-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DBU (15.0 mL, 100 mmol) was added dropwise to a solution of ethyl 3-chloro-3-methyl-1-[(4-methylphenyl)sulfonyl]prolinate (15 g, 43 mmol) in THF (100 mL). The mixture was stirred overnight at RT. Diethyl ether (100 mL) and ice cold 5% HCl (100 mL) were added, the layers separated. The organic layer was washed again with washed with ice cold 5% HCl (100 mL) and water (50 mL) followed by saturated sodium bicarbonate (100 mL) and saturated NaCl (50 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated to afford ethyl 3-methyl-1H-pyrrole-2-carboxylate (5.6 g, 84%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.42 (br. s., 1H) 6.84 (t, 1H) 6.00 (t, 1H) 4.21 (q, 2H) 2.25 (s, 3H) 1.28 (t, 3 H). MS: m/z 153.9 (M+1).

Workup

  1. customthe layers separated
  2. washThe organic layer was washed again
  3. washwith washed with ice cold 5% HCl (100 mL) and water (50 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7839e57ad2494a6aa463a7f52cfc4cf5
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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