Acetone → Methyl 1-(2-chloroethyl)-3-(methoxycarbonyl)-1H-pyrrole-2-acetate

HRID 1762998Notes

Reaction equation

HRID 1762998 reaction equation
[C:1]([O-])(=O)[CH3:2].[Na+].[Cl:6][CH2:7][CH2:8][NH:9][C:10]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:11][C:12]([O:14][CH3:15])=[O:13].CC(C)=O>O>[Cl:6][CH2:7][CH2:8][N:9]1[CH:2]=[CH:1][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]1[CH2:16][C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 180AcetoneHCID 517045Sodium AcetateHCID 740157091,5-Dimethyl 3-[(2-chloroethyl)amino]-2-pentenedioate

Product 1

HCID 14479926Methyl 1-(2-chloroethyl)-3-(methoxycarbonyl)-1H-pyrrole-2-acetateYield 90.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The hydrolysis solution was added to a mechanically-stirred slurry of sodium acetate (17.8 g, 212 mmol) in water (15 mL) at 0° C. over 1 hour, then stirred for a further 10 minutes. Dimethyl 3-(2-chloroethylamino)-2-pentenedioate (20.0 g, 85 mmol) was added, followed by acetone (50 mL), and the solution allowed to warm to room temperature and stirred for 20 hours. The resulting slurry was cooled to 0° C. and kept at that temperature for 4 hours, then filtered through a coarse frit. The precipitate was washed with water (300 mL) and dried, to give 19.9 g (90% yield) of methyl N-(2-chloroethyl)-3-methoxycarbonyl-2-pyrroleacetate as white crystals, m.p. 110°-111° C., NMR (CDCl3): δ:

Workup

  1. stirringstirred for 20 hours
  2. temperatureThe resulting slurry was cooled to 0° C.
  3. waitkept at that temperature for 4 hours
  4. filtrationfiltered through a coarse frit
  5. washThe precipitate was washed with water (300 mL)
  6. customdried

Sources & evidence

ORD record
ord-c1264fd8070e4631a08c199a823d99d0
Source dataset
uspto-grants-1989_05
Patent number
US04835288

Reaction notes

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