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

HRID 1639278Notes

Reaction equation

HRID 1639278 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, infrared (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-f37d60feaada4dc9b25ec3364300fac9
Source dataset
uspto-grants-1989_11
Patent number
US04883807

Reaction notes

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