Glycine → Methyl (1H-pyrrol-1-yl)acetate

HRID 1742016Notes

Reaction equation

HRID 1742016 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[C:6]([O-])(=O)C.[K+].CO[CH:13]1[CH2:17][CH2:16][CH:15](OC)O1.C(=O)(O)[O-].[Na+]>O.C(O)(=O)C>[N:1]1([CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH:13]=[CH:17][CH:16]=[CH:15]1

Participants

7

Reactant 4

HCID 750GlycineHCID 790982,5-DimethoxytetrahydrofuranHCID 516892Sodium BicarbonateHCID 517044Potassium Acetate

Product 1

HCID 11217296Methyl (1H-pyrrol-1-yl)acetateYield 38%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of the hydrochloride salt of the methyl ester of glycine (6.30 g) and potassium acetate (8.00 g) in water (10 ml) was added to glacial acetic acid (50 ml). The resulting mixture was heated to reflux, 2,5-dimethoxytetrahydrofuran (6.60 g) was added in one portion, and heating under reflux was continued for 4 hours. After cooling, the reaction mixture was neutralised with sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, dried, concentrated under reduced pressure, and distilled at 125° C. and ca. 15 torr using a short-path distillation apparatus to give methyl pyrrol-1-ylacetate (2.62 g, 38% yield) as a colourless liquid, infra red (film) 1750 cm-1.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. temperatureheating
  4. temperatureunder reflux
  5. temperatureAfter cooling
  6. extractionextracted with ethyl acetate
  7. washThe extracts were washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. distillationdistilled at 125° C.

Sources & evidence

ORD record
ord-06ebf1c6cd1c4e759e68eceed0f73e39
Source dataset
uspto-grants-1994_08
Patent number
US05336682

Reaction notes

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