Sodium Acetate → methyl N-(2-bromoethyl)-3-methoxycarbonyl-2-pyrroleacetate

HRID 2108215Notes

Reaction equation

HRID 2108215 reaction equation
[C:1]([O-])(=O)[CH3:2].[Na+].[Br: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]>C(O)(C)C>[Br: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

4

Reactant 2

HCID 517045Sodium AcetateHCID 74015712Dimethyl 3-(2-bromoethylamino)-2-pentenedioate

Product 1

HCID 14479925methyl N-(2-bromoethyl)-3-methoxycarbonyl-2-pyrroleacetateYield 72.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium acetate (41.0 g, 500 mmol) was added to the 2-bromoacetaaldehyde solution, and stirred for 5 minutes, at which point the solution had a pH of 6. The flask was placed in a cool tap water bath and dimethyl 3-(2-bromoethylamino)-2-pentenedioate (20.0 g, 71 mmol) was added, followed by isopropanol (40 mL), and the solution was stirred at room temperature (25° C.). Within about 35 minutes, all the solids had dissolved, and a precipitate started forming within 90 minutes. Stirring was continued at room temperature for 20 hours, and the solution then cooled to 0° C. and stirred at that temperature for 1 hour, then filtered through a coarse frit. The precipitate was washed with ice-cold water (400 mL) and ice-cold isopropanol (150 mL) and dried, to give 15.7 g (72% yield) of crude methyl N-(2-bromoethyl)-3-methoxycarbonyl-2-pyrroleacetate as a light tan solid, m.p. 129°-130.5° C.,

Workup

  1. customThe flask was placed in a cool tap water bath
  2. stirringthe solution was stirred at room temperature (25° C.)
  3. waitWithin about 35 minutes
  4. dissolutionall the solids had dissolved
  5. customa precipitate started forming within 90 minutes
  6. stirringStirring
  7. waitwas continued at room temperature for 20 hours
  8. stirringstirred at that temperature for 1 hour
  9. filtrationfiltered through a coarse frit
  10. washThe precipitate was washed with ice-cold water (400 mL) and ice-cold isopropanol (150 mL)
  11. customdried

Sources & evidence

ORD record
ord-ff24b0c8c084412eb75cab270ed21959
Source dataset
uspto-grants-1990_06
Patent number
US04937368

Reaction notes

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