Water → 65766-97-4

HRID 1391026Notes

Reaction equation

HRID 1391026 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH2:4][C:5](=O)[CH3:6].Cl.[CH3:10][O:11][C:12](=[O:15])[CH2:13][NH2:14].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[CH3:1][C:2]1[N:14]([CH2:13][C:12]([O:11][CH3:10])=[O:15])[C:5]([CH3:6])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80352,5-HexanedioneHCID 122755Glycine methyl ester hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 1350083165766-97-4

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of hexan-2,5-dione (23 g.), glycine methyl ester hydrochloride (25 g.), and sodium acetate (16 g.) in acetic acid (100 cm3) was heated under reflux for 1 hour. The mixture was then poured into water, extracted with ether, and the ethereal phase washed with sodium carbonate solution, dried, and evaporated to yield a brown oil. The product was then distilled under vacuum to give methyl (2,5-dimethyl-1H-pyrrol-1-yl)acetate as a colourless oil which crystallised on standing. (22.1 g.) b.p. 123°-129° C./15 mm, m.p. 44°-46° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. extractionextracted with ether
  3. washthe ethereal phase washed with sodium carbonate solution
  4. customdried
  5. customevaporated
  6. customto yield a brown oil
  7. distillationThe product was then distilled under vacuum

Sources & evidence

ORD record
ord-e6d5cd5d290c473d90afe91736a59f97
Source dataset
uspto-grants-1979_02
Patent number
US04140793

Reaction notes

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