Sodium Hydroxide → 3-(2,4-dimethyl-1H-pyrrol-3-yl)propanoic Acid

HRID 1372383

Reaction equation

HRID 1372383 reaction equation
C(OC([C:6]1[NH:7][C:8]([CH3:18])=[C:9]([CH2:12][CH2:13][C:14]([O:16]C)=[O:15])[C:10]=1[CH3:11])=O)C.[OH-].[Na+]>Cl>[CH3:18][C:8]1[NH:7][CH:6]=[C:10]([CH3:11])[C:9]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 291754Ethyl 4-(3-methoxy-3-oxopropyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate

Product 1

HCID 15125193-(2,4-dimethyl-1H-pyrrol-3-yl)propanoic AcidYield 49%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

4-(2-Methoxycarbonyl-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (Aldrich, 228 g, 0.9 mol) and 720 mL of 5 N sodium hydroxide were refluxed for one hour. Thin layer chromatography showed the hydrolysis to be complete. The stirred mixture was cooled to 50° C. and hydrochloric acid (10 N, 390 mL) was slowly added to give a pH of 2-3. The oil which separated solidified. The mixture was stirred and cooled to 4° C. The solids were collected by vacuum filtration, washed thoroughly with water and dried under vacuum at 40° C. to give 65.7 g (49% yield) of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid as a reddish solid.

Workup

  1. customthe hydrolysis
  2. customto give a pH of 2-3
  3. customThe oil which separated
  4. temperaturecooled to 4° C
  5. filtrationThe solids were collected by vacuum filtration
  6. washwashed thoroughly with water
  7. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-7426b3dd65634089a54120d586bb0788
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Linked notes

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